Acetic Anhydride → [(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2,5-difluorophenyl)methylidene]amino] acetate

HRID 652901Notes

Reaction equation

HRID 652901 reaction equation
[Cl:1][C:2]1[C:3]([OH:21])=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])/[C:5](=[N:14]\[OH:15])/[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[F:13].[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:15]/[N:14]=[C:5](/[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[F:13])\[C:4]1[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:2]([Cl:1])[C:3]=1[OH:21])(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1364773902-chloro-6-[(E)-C-(2,5-difluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

Product 1

HCID 136477398[(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2,5-difluorophenyl)methylidene]amino] acetate

Conditions

Temperature
60 °C

Procedure

A mixture of 19 g of E-3-chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone oxime and 10 ml of acetic anhydride was warmed at 60° C. for 30 minutes. On cooling the mixture solidifies. The residue is partitioned between ethyl acetate and 10%NaHCO3. The ethylacetate extract is washed with water, dried over Na2SO4 and evaporated to give E-3-chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone O-acetyl oxime, mp 130°-131° C.

Workup

  1. temperatureOn cooling the mixture
  2. customThe residue is partitioned between ethyl acetate and 10%NaHCO3
  3. extractionThe ethylacetate extract
  4. washis washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-86f5e4b8258a4eb2aef0570b299369fc
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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