Imidazole → N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide

HRID 1078385Notes

Reaction equation

HRID 1078385 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][C:11]([NH:13][C:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:16])[CH3:15])=[O:12]>C1COCC1>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]([NH:13][C:11](=[O:12])[CH2:10][CH2:9][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)([CH3:16])[CH3:15])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 194295363-chloro-N-[1-(4-chlorophenyl)-1-methylethyl]propionamide

Product 1

HCID 19429499N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a similar manner to Example 52c a mixture of imidazole (1.05 g) and sodium hydride (0.63 g, 60% dispersion) in THF (35 ml) was treated with 3-chloro-N-[1-(4-chlorophenyl)-1-methylethyl]propionamide (4.0 g) in THF (15 ml) to give N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide which was used directly in part (c).

Sources & evidence

ORD record
ord-ad850db23b2c4cee8e61cc5ec0bd31ca
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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