2-Methylimidazole → N-[1-(4-chlorophenyl)-1-methylethyl]-3-(2-methylimidazol-1-yl)propionamide

HRID 1078386Notes

Reaction equation

HRID 1078386 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Cl[CH2:10][CH2:11][C:12]([NH:14][C:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([CH3:17])[CH3:16])=[O:13]>C1COCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]([NH:14][C:12](=[O:13])[CH2:11][CH2:10][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])([CH3:17])[CH3:16])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 194295363-chloro-N-[1-(4-chlorophenyl)-1-methylethyl]propionamide

Product 1

HCID 19429464N-[1-(4-chlorophenyl)-1-methylethyl]-3-(2-methylimidazol-1-yl)propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a similar manner to Example 52c, a mixture of 2-methylimidazole (1.3 g) and sodium hydride (0.63 g, 60% dispersion) in THF (35 ml) was treated with a mixture of 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-(2-methylimidazol-1-yl)propionamide as an oil which was used directly in part (b) below.

Sources & evidence

ORD record
ord-0d8874ad14b64539aba79e9189f10c93
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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