Dichloroacetyl chloride → 2-Dichloroacetoxyimino-2-(isothiazol-4-yl)acetic acid

HRID 1703020Notes

Reaction equation

HRID 1703020 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[OH:7][N:8]=[C:9]([C:13]1[CH:14]=[N:15][S:16][CH:17]=1)[C:10]([OH:12])=[O:11]>C(Cl)Cl>[Cl:1][CH:2]([Cl:6])[C:3]([O:7][N:8]=[C:9]([C:13]1[CH:14]=[N:15][S:16][CH:17]=1)[C:10]([OH:12])=[O:11])=[O:4]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 571550852-Hydroxyimino-2-(isothiazol-4-yl)acetic acid

Product 1

HCID 540721882-Dichloroacetoxyimino-2-(isothiazol-4-yl)acetic acidYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloroacetyl chloride (3.58 g.) was added with stirring and ice-cooling to a suspension of 2-hydroxyimino-2-(isothiazol-4-yl)acetic acid (syn isomer) (1.50 g.) in dry methylene chloride (40 ml.), and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was concentrated to the volume of 10 ml. Petroleum ether (50 ml.) was added to the residue and the mixture was cooled in dry ice-acetone bath. Precipitates were collected by filtration and washed with petroleum ether to give 2-dichloroacetoxyimino-2-(isothiazol-4-yl)acetic acid (syn isomer) (1.20 g.).

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. concentrationThe reaction mixture was concentrated to the volume of 10 ml
  3. additionPetroleum ether (50 ml.) was added to the residue
  4. temperaturethe mixture was cooled in dry ice-acetone bath
  5. customPrecipitates
  6. filtrationwere collected by filtration
  7. washwashed with petroleum ether

Sources & evidence

ORD record
ord-4ff238e299f24119bcc5258b0dd86664
Source dataset
uspto-grants-1982_09
Patent number
US04350693

Reaction notes

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