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

HRID 1048866
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HRID 1048866 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0d42599e31154177b813de70230883bd
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382218B2

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