Clanobutin → ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)butyrate

HRID 1413583Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])[C:9]2[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:25][C:26]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:27]=1[NH:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([CH2:17][CH2:18][CH2:19][C:20]([N:28]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]2[C:37]([CH3:41])=[CH:38][CH:39]=[CH:40][C:26]=2[CH3:25])=[O:21])[C:9]2[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 35378Clanobutin

HCID 20292063Ethyl 4-(2,6-dimethylanilino)butyrate

Product 1

HCID 20292148ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)butyrate

Procedure

Analogously to Example 1, by using equivalent quantities, reacting N-(p-chlorobenzoyl)-4-(p-anisidino)-butyric acid and ethyl 4-(2,6-dimethylanilino)butyrate and suitable processing produces ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)butyrate (oil), saponification of which and the processing of the reaction product yields N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)butyric acid (M.P. 131° to 133°).

Sources & evidence

ORD record: ord-6dd7f7646b4c4b45ae7fb5edd6b59eb8
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04250183

Reaction notes

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