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

HRID 323967Notes

Reaction equation

HRID 323967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11](=C)C(N)=O)([CH3:10])C)=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[C:19]([CH:21]=[O:22])[N:18]=[CH:17]1.[OH-].[CH2:24]([N+:31](C)(C)C)[C:25]1C=CC=C[CH:26]=1.[O:35]1CCOCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:31][C:24](=[O:35])[CH2:25][CH2:26][N:16]2[CH:20]=[C:19]([CH:21]=[O:22])[N:18]=[CH:17]2)([CH3:10])[CH3:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 764281H-Imidazole-4-carbaldehydeHCID 86756612(-(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-[(-(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. 151-153° C.

Sources & evidence

ORD record
ord-d2baa66292a54d9494fb733582632ea5
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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