p-(Trifluoromethoxy)phenyl isocyanate → Ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate

HRID 499911Notes

Reaction equation

HRID 499911 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1COCC1>[CH3:7][N:5]1[CH:6]=[C:2]([NH:1][C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:17][CH:18]=2)=[O:24])[N:3]=[C:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 7006687ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 59421902Ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.22 g (3.61 mmol) of ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate (synthesis analogous to Example 4A, stage 3, or else according to Tetrahedron Lett. 2003, 44, 1607 and literature cited therein) in 50 ml of THF are mixed with 1.46 g (7.21 mmol) of 4-(trifluoromethoxy)phenyl isocyanate under argon and stirred at room temperature overnight. The reaction mixture is filtered, and the filtrate is concentrated in vacuo and purified by chromatography.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-f4ef7a9048bf4bb0b2906f4be97d0e1d
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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