1,4-Dioxane → N-[1-(4-chlorophenyl)-1-methylethyl]-3-(4-formylimidazol-1-yl)propionamide

HRID 2268255Notes

Reaction equation

HRID 2268255 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.[NH:16]1[CH:20]=[C:19]([CH:21]=[O:22])[N:18]=[CH:17]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCOCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:11][C:12](=[O:15])[CH2:13][CH2:14][N:16]2[CH:20]=[C:19]([CH:21]=[O:22])[N:18]=[CH:17]2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 764281H-Imidazole-4-carbaldehydeHCID 18349731N-[1-(4-chlorophenyl)-1-methylethyl]-acrylamide

Product 1

HCID 18349775N-[1-(4-chlorophenyl)-1-methylethyl]-3-(4-formylimidazol-1-yl)propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of N-[1-(4-chlorophenyl)-1-methylethyl]acrylamide (22.35 g), imidazole-4-carboxaldehyde (9.6 g), benzyltrimethylammonium hydroxide (2.24 ml of a 40% solution in methanol, Triton®B) and 1,4-dioxane (112 ml) was stirred and heated at 95° C. for 6 hours and then worked up as described in Example 19a to give N-[1-(4-chlorophenyl)-1-methylethyl]-3-(4-formylimidazol-1-yl) propionamide, m.p. 151-1530° C.

Sources & evidence

ORD record
ord-13772689b9d24b8195d27a888a8c7ed1
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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