Chemical process
DC CAFC
First Claim
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1. A process for the preparation of a compound of formula (I):
- wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
CCO2 CH3 ;
Z1 is a halogen atom; and
R1, R2, R3 and R4 are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, acetoxy or acyl;
the process comprising the steps of;
(a) reacting a compound of formula (II);
##STR5## wherein R1, R2, R3 and R4 are as defined above, with a compound of formula ROCH3, wherein R is a metal; and
,(b) reacting the product of (a) with a compound of formula (III);
##STR6## wherein Z1 and Z2 are halogen atoms.
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Abstract
A process for the preparing agrochemical intermediates of formula (I): ##STR1## wherein W is (CH3 O) CH.CHCO2 CH3 or CH3 O.CH═CCO2 CH3 ; Z1 is a halogen atom; and R1, R2, R3 and R4 are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, acetoxy or acyl; the process comprising the steps of:
(a) reacting a compound of formula (II): ##STR2## wherein X, R1, R2, R3 and R4 are as defined above, with a compound of formula ROCH3, wherein R is a metal; and,
(b) reacting the product of (a) with a compound of formula (III): ##STR3## wherein Z1 and Z2 are halogen atom. A process for the preparation of compounds of formula (II) and compounds of formula (II) themselves. A process for obtaining, in substantially pure form, a compound of formula (II) wherein R1, R2, R3 and R4 are all hydrogen.
10 Citations
16 Claims
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1. A process for the preparation of a compound of formula (I):
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wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
CCO2 CH3 ;
Z1 is a halogen atom; and
R1, R2, R3 and R4 are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, acetoxy or acyl;
the process comprising the steps of;(a) reacting a compound of formula (II);
##STR5## wherein R1, R2, R3 and R4 are as defined above, with a compound of formula ROCH3, wherein R is a metal; and
,(b) reacting the product of (a) with a compound of formula (III);
##STR6## wherein Z1 and Z2 are halogen atoms. - View Dependent Claims (7, 10, 11)
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2. A process for the preparation of a compound of general formula (IV):
- ##STR7## wherein Z1 is a halogen atom;
the process comprising reacting a compound of formula (X);
##STR8## with a compound of general formula (III);
##STR9## wherein Z1 is as defined above and Z2 is a halogen atom, in the presence of a methoxide anion.
- ##STR7## wherein Z1 is a halogen atom;
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3. A process for the preparation of a general formula (IV):
- ##STR10## wherein Z1 is a halogen atom;
the process, which is carried out in the presence of methanol, comprising the steps of;(a) reacting a compound of formula (X);
##STR11## with a compound of formula ROCH3, wherein R is a metal; and
, (b) reacting the product of (a) with a compound of general formula (III);
##STR12## wherein Z1 is as defined above, and Z2 is a halogen atom.
- ##STR10## wherein Z1 is a halogen atom;
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4. A process for the preparation of a compound of general formula (V):
- ##STR13## wherein Z1 is a halogen atom;
the process comprising the steps of;
a) reacting a compound of formula (X);
##STR14## with a compound of formula ROCH wherein R is a metal; and
b) reacting the product formed in (a) with a compound of general formula (III);
##STR15## wherein Z1 is as defined above and Z2 is a halogen atom.
- ##STR13## wherein Z1 is a halogen atom;
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5. A process for the preparation of a compound of formula (I):
- ##STR16## wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
CCO2 CH3 ;
Z1 is a halogen atom; and
R1, R2, R3 and R4 are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, acetoxy or acyl;
the process comprising the steps of;(a) reacting a compound of formula (II);
##STR17## wherein R1, R2, R3 and R4 are as defined above, with a compound of formula ROCH3, wherein R is a metal; and
,(b) reacting the product of (a) with a compound of formula (III);
##STR18## wherein Z1 and Z2 are halogen atoms;
step (b) being carried out in the presence of methanol.
- ##STR16## wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
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6. A process for the preparation of a compound of formula (VI):
- ##STR19## and stereoisomers thereof, wherein R1, R2, R3 and R4 are independently hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, acetoxy or acyl; and
Y and Z are, independently, hydrogen, halogen, cyano, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, CSNH2, CONH2 or nitro;
the process comprising the steps of;a) reacting a compound of formula (II);
##STR20## wherein R1, R2, R3 and R4 are as defined above;
with a compound of formula ROCH3 wherein R is a metal;b) reacting the product of (a) with a compound of formula (III);
##STR21## wherein Z1 and Z2 are halogen atoms; and
1) (c) eliminating methanol from the compound of formula (I);
##STR22## wherein Z1 is a halogen atom;
R1, R2, R3 and R4 are as defined above, and W is (CH3 O)2 CHCHCO2 CH3, in the mixture of products from (b); and(d) reacting the product of (c) with a compound of formula (VII);
##STR23## wherein Z and Y are as defined above;
or
2) (c) reacting the product of (b) with a compound of formula (VII);
##STR24## wherein Z and Y are as defined above; and
(d) (i) separating the compound of formula (VI);
or(ii) eliminating methanol from the compound of formula (VIII);
##STR25## wherein R1, R2, R3, R4, Y and Z are as defined above, in the mixture of products from (c);
or(iii) separating a compound of formula (VIII) from the mixture of products from (c) and eliminating methanol from it;
or3) (c) separating the compounds of formula (I), wherein W is (CH3 O)2 CHCHCO2 CH3 and CH3 O.CH═
CCO2 CH3, in the mixture of products from (b); and(d) (i) reacting the compound of formula (I), wherein W is CH3 O.CH═
CCO2 CH3, with a compound of formula (VII);
##STR26## wherein Y and Z are defined above;
or (ii) reacting the compound of formula (I), wherein W is (CH3 O)2 CHCHCO2 CH3, with a compound of formula (VII);
##STR27## and eliminating methanol from the product so formed;
or (iii) eliminating methanol from the compound of formula (I), wherein W is (CH3 O)2 CHCHCO2 CH3, and reacting the product so formed with a compound of formula (VII);
##STR28## wherein Y and Z are as defined above. - View Dependent Claims (12, 13, 14)
- ##STR19## and stereoisomers thereof, wherein R1, R2, R3 and R4 are independently hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, acetoxy or acyl; and
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8. A process for the preparation of a compound of formula (I):
- ##STR29## wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
CCO2 CH3 ;
Z1 is a halogen atom; and
R1, R2, R3 and R4 are independently hydrogen, C1 -C4 alkyl, C1 -4 alkoxy, acetoxy or acyl;
the process comprising the steps of;i) (a) reacting a compound of formula (XWV);
##STR30## wherein R1, R2, R3 and R4 are as defined above, with trimethyl orthoformate;(b) reacting the product of step (a) with a compound of formula ROCH3, wherein R is a metal; and
,(c) reacting the product of step (b) with a compound of formula (III);
##STR31## wherein Z1 and Z2 are halogen atoms;
or ii) (a) reacting a compound of formula (XIV);
##STR32## wherein R1, R2, R3 and R4 are as defined above, with a dimethoxymethyl carboxylate;(b) reacting the product of step (a) with a compound of formula ROCH3, wherein R is a mental; and
,(c) reacting the product of step (b) with a compound of formula (III);
oriii) (a) cyclising a compound of formula (IX);
##STR33## wherein R1, R2, R3 and R4 are as defined above, and reacting the product formed with either trimethyl orthofornate or a dimethoxymethyl carboxylate;(b) reacting the product of step (a) with a compound of formula ROCH3, wherein R is a metal; and
,(c) reacting the product of step (b) with a compound of formula (III). - View Dependent Claims (9, 15, 16)
- ##STR29## wherein W is (CH3 O)2 CH.CHCO2 CH3 or CH3 O.CH═
Specification
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Litigation Data
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Current AssigneeSyngenta Limited (China National Chemical Corporation)
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Original AssigneeImperial Chemical Industries PLC (IMPERIAL CHEMICAL INDUSTRIES)
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InventorsWilkinson, Paul, Fielden, Jan Michael, Jones, John David, Cox, Brian Geoffrey, DeBoos, Gareth Andrew
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Primary Examiner(s)Gupta, Yogendra N.
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Application NumberUS08/479,242Time in Patent Office1,280 DaysField of Search544/298, 544/319US Class Current544/319CPC Class CodesC07D 239/34 One oxygen atomC07D 307/83 Oxygen atomsC07D 311/12 substituted in position 3 a...
