Ethyl 4-(2,6-dimethylanilino)butyrate → ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-4-(2,6-dimethylanilino)butyrate

HRID 1413590Notes

Reaction equation

HRID 1413590 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][C:18]([OH:20])=O)[C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:25]=1[NH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][C:18]([N:26]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]2[C:35]([CH3:39])=[CH:36][CH:37]=[CH:38][C:24]=2[CH3:23])=[O:20])[C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 20292063Ethyl 4-(2,6-dimethylanilino)butyrateHCID 20292207N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetic acid

Product 1

HCID 20292231ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-4-(2,6-dimethylanilino)butyrate

Procedure

Analogously to Example 1, by using equivalent quantities, reacting N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetic acid and ethyl 4-(2,6-dimethylanilino)butyrate and suitable processing produces ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-4-(2,6-dimethylanilino)butyrate (M.P. 150° to 151°), saponification of which and processing of the reaction product yields N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-4-(2,6-dimethylanilino) butyric acid (M.P. 214° to 216°).

Sources & evidence

ORD record
ord-53de29a8e48f432caeb16d72f77adf74
Source dataset
uspto-grants-1981_02
Patent number
US04250183

Reaction notes

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