Carbon Dioxide → 2-Chloro-4-fluoro-5-isothiocyanatothiobenzoic acid (methoxycarbonylmethyl) ester

HRID 1033216Notes

Reaction equation

HRID 1033216 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[S:17])[C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([F:15])=[CH:10][C:9]=1[Cl:16])=[O:4].C(=O)([O-])[O-].[Ca+2].[C:23](Cl)(Cl)=[S:24].C(=O)=O>ClCCl.O>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[S:17])[C:8]1[CH:13]=[C:12]([N:14]=[C:23]=[S:24])[C:11]([F:15])=[CH:10][C:9]=1[Cl:16])=[O:4]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 539902175-Amino-2-chloro-4-fluorothiobenzoic acid (methoxycarbonylmethyl) ester

Product 1

HCID 538361362-Chloro-4-fluoro-5-isothiocyanatothiobenzoic acid (methoxycarbonylmethyl) ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.8 g of the resulting 5-amino-2-chloro-4-fluorothiobenzoic acid (methoxycarbonylmethyl) ester in 100 ml of dichloromethane is added dropwise at from 25° to 30° C. to a suspension of 6 g of calcium carbonate, 4 ml of thiophosgene, 20 ml of dichloromethane and 20 ml of water. When the evolution of carbon dioxide has ceased, the batch is stirred for a further 18 hours at room temperature. After filtering and washing with water, the organic phase is separated off, dried over sodium sulfate and then concentrated by evaporation to yield 4.8 g of 2-chloro-4-fluoro-5-isothiocyanatothiobenzoic acid (methoxycarbonylmethyl) ester in the form of an oil which is used without further purification in the next reaction step.

Workup

  1. filtrationAfter filtering
  2. washwashing with water
  3. customthe organic phase is separated off
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2b6338f223734276899fff354bb08cc9
Source dataset
uspto-grants-1994_05
Patent number
US05310722

Reaction notes

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