Hydrochloric Acid → N-(2'-chloro-4'-isothiocyanato-6'-(trifluoromethyl)biphenyl-3-yl)methanesulfonamide

HRID 1048866Notes

Reaction equation

HRID 1048866 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:13]=2)=[C:4]([Cl:23])[CH:3]=1.C(=O)([O-])[O-].[Ca+2].[C:29](Cl)(Cl)=[S:30].Cl>ClCCl.O>[Cl:23][C:4]1[CH:3]=[C:2]([N:1]=[C:29]=[S:30])[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 90390781HCID 90390781, compound

Product 1

HCID 90390276N-(2'-chloro-4'-isothiocyanato-6'-(trifluoromethyl)biphenyl-3-yl)methanesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) suspension of N-(4′-amino-2′-chloro-6′-(trifluoromethyl)biphenyl-3-yl)methanesulfonamide (570 mg, 1.56 mmol, Eq: 1.00) and calcium carbonate (313 mg, 3.13 mmol, Eq: 2) in dichloromethane (3.38 ml) and water (3.38 ml) was added thiophosgene (198 mg, 131 μl, 1.72 mmol, Eq: 1.1). The reaction mixture was allowed to warm up to room temperature and was vigorously stirred for 16 h. 1N HCl was added to adjust the pH to ca. 2. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and washed with water then brine and purified on silica gel (column 24 g, dichloromethane/ethyl acetate 1:0 to 85:15) to give 565 mg (89%) of the desired product as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. custombrine and purified on silica gel (column 24 g, dichloromethane/ethyl acetate 1:0 to 85:15)

Sources & evidence

ORD record
ord-0d42599e31154177b813de70230883bd
Source dataset
uspto-grants-2016_07
Patent number
US09382218B2

Reaction notes

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