Benzoyl isothiocyanate → HCID 21397156, compound

HRID 1439370Notes

Reaction equation

HRID 1439370 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:4][CH2:3]1.[C:19]([N:27]=[C:28]=S)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]=[C:28]2[NH:27][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 14319495HCID 14319495, compound

Product 1

HCID 21397156HCID 21397156, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[3-(4-methyl-1-piperazinyl)propyl]-o-phenylenediamine (1.24 g., 0.005 mole) in ethanol (50 ml.) was added 0.82 g. (0.005 mole) benzoyl isothiocyanate in one portion. After stirring overnight at room temperature, the solution was evaporated in vacuo to a red oil, which was chromatographed on a silica gel column yielding on crystallization from ethyl acetate 390 mg. of 1-[3-(4-methyl-1-piperazinyl)propyl]-2-benzamido-benzimidazole (yield 20.6%), m.p. 147°-148° C. The material isolated by this synthesis was identical in all respects to an authentic sample.

Workup

  1. customthe solution was evaporated in vacuo to a red oil, which
  2. customwas chromatographed on a silica gel column
  3. customyielding on crystallization from ethyl acetate 390 mg

Sources & evidence

ORD record
ord-8234ab2f640c4c83926763854770e808
Source dataset
uspto-grants-1977_11
Patent number
US04059584

Reaction notes

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