Benzoyl isothiocyanate → HCID 59426163, compound

HRID 907192Notes

Reaction equation

HRID 907192 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)[CH:5]=[CH:6][CH:7]=1.[C:23]([N:31]=[C:32]=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:23]([NH:31][C:32]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)[CH:3]=1)=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 59425429HCID 59425429, compound

Product 1

HCID 59426163HCID 59426163, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The starting material 2-(3-amino-phenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (187 mg, 0.642 mmol) was dissolved in anhydrous acetone (3.0 mL). Benzoyl isothiocyanate (107 mg, 0.656 mmol) was added to the solution at room temperature and the mixture was stirred for 17 h during which time a precipitate had formed. The precipitate was filtered, washed with acetone and dried to give 264 mg of 1-benzoyl-3-[3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-thiourea (90% yield) as a light yellow solid.

Workup

  1. customhad formed
  2. filtrationThe precipitate was filtered
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-3c2ee6a4668e49f592be7b1e3012ecb2
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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