1,2-Dichloroethane → 2-(2-Chloro-4-fluoro-5-isothiocyanatophenylthio)-cyclobutanecarboxylic acid methyl ester

HRID 1646453Notes

Reaction equation

HRID 1646453 reaction equation
COC([C:5]1([S:9][C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([F:17])=[CH:12][C:11]=2[Cl:18])[CH2:8][CH2:7][CH2:6]1)=O.[C:19](=[O:22])([O-])[O-:20].[Ca+2].[C:24](Cl)(Cl)=[S:25].[CH2:28](Cl)CCl>O>[CH3:28][O:20][C:19]([CH:8]1[CH2:7][CH2:6][CH:5]1[S:9][C:10]1[CH:15]=[C:14]([N:16]=[C:24]=[S:25])[C:13]([F:17])=[CH:12][C:11]=1[Cl:18])=[O:22]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 544812611-(5-Amino-2-chloro-4-fluorophenylthio)-cyclobutanecarboxylic acid methyl ester

Product 1

HCID 538062772-(2-Chloro-4-fluoro-5-isothiocyanatophenylthio)-cyclobutanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While stirring at a temperature of from +25° to +30° C., a solution of 12 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclobutanecarboxylic acid methyl ester obtained in accordance with Example P1 in 30 ml of ethylene chloride is added dropwise to a mixture of 12 g of calcium carbonate and 8 ml of thiophosgene in 40 ml of ethylene chloride and 40 ml of water. The reaction mixture is then stirred for 18 hours. After filtering off the resulting precipitate, the organic phase is dried over calcium chloride and then concentrated in vacuo, yielding 13.1 g of 2-(2-chloro-4-fluoro-5-isothiocyanatophenylthio)-cyclobutanecarboxylic acid methyl ester in the form of an oil.

Workup

  1. stirringThe reaction mixture is then stirred for 18 hours
  2. filtrationAfter filtering off the resulting precipitate
  3. dry with materialthe organic phase is dried over calcium chloride
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4862b5fcdb6841f3879ef3bb6ca988e5
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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