Methyl Isocyanate → HCID 178485942, compound

HRID 1370136Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=3[N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=3)[C:9]2=[O:29])[CH2:4][CH2:3]1.[CH3:30][N:31]=[C:32]=[O:33]>ClCCl>[Cl:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][N:10]1[C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=2[N:8]([C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][C:32]([NH:31][CH3:30])=[O:33])[CH2:3][CH2:4]2)[C:9]1=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-(trans-4-aminocyclohexyl)-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (100 mg) and methyl isocyanate (17 mg) in dichloromethane (3 mL) was stirred at 0° C. for 2 hours under nitrogen atmosphere. The mixture was partitioned between water and a mixture of chloroform and methanol (5:1). The separated organic layer was washed with water and dried over magnesium sulfate. After evaporation of the solvent, the residue was subjected to a preparative thin-layer chromatography eluting with a mixture of chloroform and methanol (10:1). The obtained substance was triturated with diethyl ether to give 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[trans-4-(3-methylureido)cyclohexyl]-2,3-dihydro-1H-benzimidazol-2-one (69 mg) as colorless powders.

Workup

customThe mixture was partitioned between water
additiona mixture of chloroform and methanol (5:1)
washThe separated organic layer was washed with water
dry with materialdried over magnesium sulfate
customAfter evaporation of the solvent
washeluting with a mixture of chloroform and methanol (10:1)
customThe obtained substance was triturated with diethyl ether

Sources & evidence

ORD record: ord-ce269b92319a4c81a1124e9f020bc7e4
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06582351B1

Reaction notes

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