Benzoyl isothiocyanate → 1-Benzoyl-3-(2-(3,3-dimethylindolin-1-yl)phenyl)thiourea

HRID 2192220노트

반응식

HRID 2192220 반응식
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])[CH2:3]1.[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:19]([NH:27][C:28]([NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:18])([CH3:1])[CH2:3]1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 593377202-(3,3-Dimethyl-2,3-dihydro-1H-indol-1-yl)aniline

생성물 1

HCID 593377231-Benzoyl-3-(2-(3,3-dimethylindolin-1-yl)phenyl)thiourea수율 112.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2e (40 mg, 0.168 mmol) in CH2Cl2 was added benzoyl isothiocyanate (30 mg, 0.189 mmol). The reaction mixture was kept at reflux for 2.5 h. The reaction mixture was filtered through a cake of Celite® and washed the cake with CH2Cl2. The solvent was evaporated under reduced pressure. The desired product was purified by column chromatography using 0 to 80% EtOAc in hexane over 60 min as eluting gradient to afford 2f (76 mg, 99%) as a powder. MS (ES) m/z 402 [M+H]+.

후처리

  1. temperatureat reflux for 2.5 h
  2. filtrationThe reaction mixture was filtered through a cake of Celite®
  3. washwashed the cake with CH2Cl2
  4. customThe solvent was evaporated under reduced pressure
  5. customThe desired product was purified by column chromatography
  6. customover 60 min
  7. washas eluting gradient

출처 및 근거

ORD 기록
ord-ce8052d5eb614f5a9c7c4602720a0e89
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329718B2

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