Acetyl chloride → 1-(5-Acetylthiophen-2-yl)propan-2-yl 4-methylbenzene-1-sulfonate

HRID 1381260Notes

Reaction equation

HRID 1381260 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH:11]([CH3:18])[CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:20](Cl)(=[O:22])[CH3:21].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[C:20]([C:15]1[S:14][C:13]([CH2:12][CH:11]([O:10][S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH3:18])=[CH:17][CH:16]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 2547331-Thiophen-2-ylpropan-2-yl 4-methylbenzenesulfonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 233239051-(5-Acetylthiophen-2-yl)propan-2-yl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(p-Toluenesulphonyloxy)propylthiophene (J. Org. Chem. 36, 1971, 2236) was reacted with acetyl chloride and aluminium trichloride in methylene chloride to give 5-acetyl-2-(p-toluenesulphonyloxy)propylthiophene. Therefrom there was obtained with sodium azide in dimethyl sulphoxide 5-(3-azidopropyl)-2-thienyl methyl ketone. Oxidation with hypobromide gave 5-(3-azidopropyl)-2-thiophenecarboxylic acid of melting point 71°-72°. Reaction of this acid with thionyl chloride and subsequent treatment with concentrated ammonia gave 5-(3-azidopropyl)-2-thiophenecarboxamide of melting point 85°-87°. Therefrom there is obtained, after treatment with triphenylphosphine and hydrolysis (J. Org. Chem. 40, 1975, 1659), 5-(3-aminopropyl)-2-thiophenecarboxamide of melting point 143.5°-144° (from water).

Sources & evidence

ORD record
ord-a07724bb4ca849418641ebc9565a00dd
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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