Methyl Isocyanate → HCID 13653890, compound

HRID 280354Notes

Reaction equation

HRID 280354 reaction equation
[N:1]([CH3:4])=[C:2]=[O:3].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20][C:21]3[N:25]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:24]4[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=4[N:22]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1>O1CCCC1>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][N:25]2[C:24]3[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=3[N:22]=[C:21]2[NH:20][CH:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:2]([NH:1][CH3:4])=[O:3])=[CH:7][CH:8]=3)[CH2:19][CH2:18]2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 12891722HCID 12891722, compound

Product 1

HCID 13653890HCID 13653890, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.6 parts of isocyanatomethane, 4.43 parts of N-[1-[2-(4-aminophenyl)ethyl]-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine and 135 parts of tetrahydrofuran was stirred for 3 hours at room temperature. The precipitated product was filtered off and crystallized from acetonitrile, yielding 2 parts (39.9%) of N-[4-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]phenyl]-N'methylurea; mp. +300° C. (compound 57).

Workup

  1. filtrationThe precipitated product was filtered off
  2. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-cf7f648da16a4b96b8bda9dfb5309b4e
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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