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

HRID 568662Notes

Reaction equation

HRID 568662 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]=[CH:10][CH:9]=[C:8]([F:12])[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]=[CH:10][CH:9]=[C:8]([F:12])[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 1364773892-chloro-6-[(E)-C-(2,3-difluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

Product 1

HCID 136477386[(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2,3-difluorophenyl)methylidene]amino] acetate

Conditions

Temperature
60 °C

Procedure

A mixture of 1.5 g of E-3-chloro-2',3'-difluoro-2-hydroxy-4-methoxybenzophenone oxime and 0.67 g of acetic anhydride are warmed at 60° C. for 30 minutes. The mixture is dissolved and then solidifies. The residue is partitioned between ethyl acetate and 10% NaHCO3. The ethyl acetate extract is washed, dried over Na2SO4 and evaporated to give E-3-chloro-2',3'-difluoro-2-hydroxy-4-methoxybenzophenone O-acetyl oxime, mp 136°-139° C.

Workup

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

Sources & evidence

ORD record
ord-14e43cea24394faea139597eb1923e7e
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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