Benzyltrimethylammonium hydroxide → N-[1-(4-chlorophenyl)-1-methylethyl]-3-(2-isopropylimidazol-1-yl)propionamide

HRID 1078405Notes

Reaction equation

HRID 1078405 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:16]([C:19]1[NH:20][CH:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:11][C:12](=[O:15])[CH2:13][CH2:14][N:20]2[CH:21]=[CH:22][N:23]=[C:19]2[CH:16]([CH3:18])[CH3:17])([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 18349731N-[1-(4-chlorophenyl)-1-methylethyl]-acrylamide

Product 1

HCID 19429470N-[1-(4-chlorophenyl)-1-methylethyl]-3-(2-isopropylimidazol-1-yl)propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a similar manner to Example 68a (alternative procedure), a mixture of N-[1-(4-chlorophenyl)-1methylethyl]acrylamide (6.7 g), 2-isopropylimidazole (3.3 g), 1,4-dioxane (100 ml) and benzyltrimethyl-ammonium hydroxide (Triton B) (5 ml of 40% solution in methanol) gave N-[1-(4-chlorophenyl)-1-methylethyl]-3-(2-isopropylimidazol-1-yl)propionamide as an oil not distilled.

Sources & evidence

ORD record
ord-d35ecad215144a2d9f275976f9cd3d67
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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