Fluorine → HCID 11034512, compound

HRID 1948548Notes

Reaction equation

HRID 1948548 reaction equation
FF.[N+:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[C-:4].[H-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](/[N:20]=[C:21](\Cl)/[C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:21]([C:22]([F:23])([F:24])[F:25])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:4]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 24524FluorineHCID 24758Sodium hydrideHCID 533707Ethyl isocyanoacetateHCID 178506324HCID 178506324, compound

Product 1

HCID 11034512HCID 11034512, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The synthetic intermediate imine (Z)—N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride (a pale yellow oil) was prepared as described in Huang et al., J. Fluorine Chem., 74:279-282 (1995) and used without distillation. To ethyl isocyanoacetate (0.467 g, 4.13 mmol) in dry THF (50 mL) was added NaH (170 mg, 4.13 mmol, 60% dispersed in oil) at 0° C. and after 5 minutes, (Z)—N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride (1.0 g, 4.13 mmol). The reaction mixture was allowed to warm to room temperature. The mixture was purified using an 80 g SiO2 column and a 10-100% EtOAc/hexanes gradient. Obtained 900 mg (68% yield) of ethyl 1-(4-chlorophenyl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate as a pale yellow solid. This compound matched the 1H NMR found in the J. Fluorine Chem. reference.

Workup

  1. distillation, 74:279-282 (1995) and used without distillation
  2. customThe mixture was purified

Sources & evidence

ORD record
ord-ad1da207bf8c4d108635536318d871bf
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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