Methyl Isocyanate → HCID 12044471, compound

HRID 1860191Notes

Reaction equation

HRID 1860191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([NH2:11])=[O:10])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH3:21][N:22]=[C:23]=[O:24]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([NH:11][C:23]([NH:22][CH3:21])=[O:24])=[O:10])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18626619HCID 18626619, compound

Product 1

HCID 12044471HCID 12044471, compoundYield 58,638.301%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionamide (200 mg, 0.67 mmol) and methyl isocyanate (382 mg, 6.70 mmol) in toluene (3 mL) was heated under reflux (120° C.) for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 2/1 hexanes/ethyl acetate) afforded 1-[2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (139 g, 60%) as a white foam: mp 61-64° C. (foam to gel); FAB-HRMS m/e calcd for C16H20ClN3O4 (M+H)+354.1220, found 354.1232.

Workup

  1. temperatureto cool to 25° C.
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbd8203a85e34fc0bff1663f865ded11
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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