Hydrochloric Acid → HCID 17859026, compound

HRID 1372666Notes

Reaction equation

HRID 1372666 reaction equation
C(=O)([O-])[O-].[Ca+2].[C:6](Cl)(Cl)=[S:7].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]=1[Cl:22].Cl>C(Cl)Cl.O.C(Cl)Cl>[Cl:22][C:12]1[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:16][C:11]=1[N:10]=[C:6]=[S:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 17859026HCID 17859026, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

Calcium carbonate (626 mg, 6.25 mmol) and thiophosgene (191 μl, 2.51 mmol) were suspended in methylene chloride-water (10 ml, 1:1, v/v). To the resulting suspension was added a solution of methyl 4-amino-3-chlorophenylacetate (500 mg, 2.50 mmol) in methylene chloride (5 ml) under stirring at 0° C. The temperature of the reaction mixture was raised from 0° C. to room temperature over 1.5 hours. The reaction mixture was acidified with 1N HCl, followed by extraction with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent to give methyl 3-chloro-4-isothiocyanatophenylacetate (652 mg, 100%) as a yellow oil.

Workup

  1. temperatureThe temperature of the reaction mixture was raised from 0° C. to room temperature over 1.5 hours
  2. extractionfollowed by extraction with methylene chloride
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-b67652b15db64957ac1aed04132eb00d
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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