2,5-Hexanedione → HCID 19809174, compound

HRID 973765Notes

Reaction equation

HRID 973765 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=1.[CH2:13]([CH2:17][C:18](=O)[CH3:19])[C:14]([CH3:16])=O>>[CH3:19][C:18]1[N:1]([CH2:2][CH2:3][CH2:4][C:5]2[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=2)[C:14]([CH3:16])=[CH:13][CH:17]=1

Participants

3

Reactant 2

HCID 80352,5-HexanedioneHCID 198091145-(3-Aminopropyl)thiophene-2-carboxamide

Product 1

HCID 19809174HCID 19809174, compound

Procedure

5-(3-Aminopropyl)-2-thiophenecarboxamide is reacted with acetonylacetone to give 5-[3-(2,5-dimethylpyrrol-1-yl)propyl]-2-thiophenecarboxamide, m.p. 144°-146° C. (see J. Chem. Soc. Chem. Commun. 800 [1982]). This is alkylated with n-butyl bromide to give N-butyl-5-[3-(2,5-dimethylpyrrol-1-yl)propyl]-2-thiophenecarboxamide (see Synthesis 266 [1976]). The latter is cleaved with hydroxylamine hydrochloride to give 5-(3-aminopropyl)-N-butyl-2-thiophenecarboxamide.

Sources & evidence

ORD record
ord-0cbac858262c48bb9a29fa7d9c91b370
Source dataset
uspto-grants-1991_11
Patent number
US05064863

Reaction notes

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