Methyl isothiocyanate → HCID 13769721, compound

HRID 979950Notes

Reaction equation

HRID 979950 reaction equation
[N:1]([CH3:4])=[C:2]=[S:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH:31][C:32]3[S:33][CH:34]=[CH:35][N:36]=3)[CH2:25][CH2:24]2)=[CH:8][CH:7]=1>O1CCCC1>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[NH:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][N:31]([C:32]3[S:33][CH:34]=[CH:35][N:36]=3)[C:2]([NH:1][CH3:4])=[S:3])[CH2:27][CH2:28]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 13769658HCID 13769658, compound

Product 1

HCID 13769721HCID 13769721, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.1 parts of isothiocyanatomethane, 6.76 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[2-thiazolylamino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine and 90 parts of tetrahydrofuran was stirred and refluxed for one week. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from methanol, yielding 3.5 parts (44.5%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N'-methyl-N-(2-thiazolyl)thiourea; mp. 188.5° C. (compound 104).

Workup

  1. temperaturerefluxed for one week
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-e79fc82601724d68b5a5fdd78021f7da
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

Loading…