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

HRID 2192220Notes

Reaction equation

HRID 2192220 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-ce8052d5eb614f5a9c7c4602720a0e89
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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