Butyl isocyanate → HCID 20298821, compound

HRID 1389320Notes

Reaction equation

HRID 1389320 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]([CH3:23])[C:20]([NH2:22])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:32]([CH2:35][CH2:36][CH2:37][CH3:38])=[C:33]=[O:34]>O1CCCC1>[CH2:35]([NH:32][C:33]([NH:22][C:20]1[N:19]([CH3:23])[C:18]2[CH:24]=[CH:25][C:15]([CH2:14][N:11]3[CH2:12][CH2:13][N:8]([CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:9][CH2:10]3)=[CH:16][C:17]=2[N:21]=1)=[O:34])[CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 20298830HCID 20298830, compound

Product 1

HCID 20298821HCID 20298821, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.1 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazol-2-amine, 1 part of 1-isocyanatobutane and 180 parts of tetrahydrofuran is stirred and refluxed over week-end. After cooling to room temperature, the reaction mixture is filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from ethanol. The product is filtered off, washed with ethanol and with 2,2'-oxybispropane, and dried, yielding 3.4 parts (66.7%) of N-butyl-N'-{5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazol-2-yl}urea; mp. 195.8° C.

Workup

  1. temperaturerefluxed over week-end
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from ethanol
  9. filtrationThe product is filtered off
  10. washwashed with ethanol and with 2,2'-oxybispropane
  11. customdried

Sources & evidence

ORD record
ord-96364ec2979b4a8ba115b3c2e1941021
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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