Thiophosgene → 1-(2-Chloro-4-fluoro-5-isothiocyanato-phenylthio)-cyclopropanecarboxylic acid methyl ester

HRID 1646467Notes

Reaction equation

HRID 1646467 reaction equation
[CH3:1][O:2][C:3]([C:5]1([S:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([F:16])=[CH:11][C:10]=2[Cl:17])[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[Ca+2].[C:23](Cl)(Cl)=[S:24]>C(Cl)CCl.O>[CH3:1][O:2][C:3]([C:5]1([S:8][C:9]2[CH:14]=[C:13]([N:15]=[C:23]=[S:24])[C:12]([F:16])=[CH:11][C:10]=2[Cl:17])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 54364994HCID 54364994, compound

Product 1

HCID 545373801-(2-Chloro-4-fluoro-5-isothiocyanato-phenylthio)-cyclopropanecarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

While stirring at room temperature, a solution of 5.5 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclopropanecarboxylic acid methyl ester in 20 ml of ethylene chloride is added dropwise to a mixture of 3 g of calcium carbonate, 2 ml of thiophosgene in 20 ml of ethylene chloride and 20 ml of water. After stirring for 4 hours at room temperature, the inorganic portion of the reaction mixture is filtered off and the organic phase is dried over calcium chloride and then concentrated by evaporation, yielding 6.3 g of 1-(2-chloro-4-fluoro-5-isothiocyanato-phenylthio)-cyclopropanecarboxylic acid methyl ester having a melting point of from +100° to +101° C.

Workup

  1. stirringAfter stirring for 4 hours at room temperature
  2. filtrationthe inorganic portion of the reaction mixture is filtered off
  3. dry with materialthe organic phase is dried over calcium chloride
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f5712137e94243649ca02083702274cb
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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