3-(Trifluoromethyl)phenyl isocyanate → HCID 68425438, compound

HRID 1818936Notes

Reaction equation

HRID 1818936 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:14]([O:18][C:19](=[O:30])[NH:20][CH2:21][CH2:22][N:23]1[CH:27]=[C:26]([NH2:28])[N:25]=[C:24]1[CH3:29])([CH3:17])([CH3:16])[CH3:15]>ClCCl>[C:14]([O:18][C:19](=[O:30])[NH:20][CH2:21][CH2:22][N:23]1[CH:27]=[C:26]([NH:28][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=2)=[O:11])[N:25]=[C:24]1[CH3:29])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 68425482HCID 68425482, compound

Product 1

HCID 68425438HCID 68425438, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethylphenyl isocyanate (0.23 g, 1.2 mmol) was added to a solution of compound 40.2 (0.30 g, 1.2 mmol) in dichloromethane (5 mL). The reaction mixture was stirred for 15 minutes, concentrated and purified by flash column chromatography on silica gel using EtOAc to provide (2-{2-methyl-4-[3-(3-trifluoromethyl-phenyl)-ureido]-imidazol-1-yl}-ethyl)-carbamic acid tert-butyl ester (compound 40.3; 0.11 g, 21%). ES (+) MS m/e=428(M+1).

Workup

  1. concentrationconcentrated
  2. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-783ffaf33af845089e60fbe2815b8ee2
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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