1,2-Benzenediamine, N-[(4-fluorophenyl)methyl]- → N-{2-[(4-fluorophenylmethyl)amino]phenyl}-N'-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]thiourea

HRID 1856582Notes

Reaction equation

HRID 1856582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N:27]=[C:26]2[NH:34][CH:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][N:43]=[C:44]=[S:45])[CH2:37][CH2:36]2)=[CH:20][CH:19]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:44]([NH:43][CH2:42][CH2:41][N:38]2[CH2:39][CH2:40][CH:35]([NH:34][C:26]3[N:25]([CH2:24][C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[N:27]=3)[CH2:36][CH2:37]2)=[S:45])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 114699771,2-Benzenediamine, N-[(4-fluorophenyl)methyl]-HCID 128917531-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]1H-benzimidazol-2-amine

Product 1

HCID 53996556N-{2-[(4-fluorophenylmethyl)amino]phenyl}-N'-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]thioureaYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.1 parts of N-(4-fluorophenylmethyl)-1,2-benzenediamine, 4 parts of 1-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine and 90 parts of tetrahydrofuran is stirred and refluxed for 2 hours. The reaction mixture is evaporated, yielding 6 parts (100%) of N-{2-[(4-fluorophenylmethyl)amino]phenyl}-N'-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}-ethyl]thiourea as a residue.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-5b2512c969144d60948eb41b1843f992
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

Loading…