Triphenylphosphine → 5-(2-Aminoethyl)thiophene-2-carboxamide

HRID 1906661Notes

Reaction equation

HRID 1906661 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[NH2:1][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 198091795-(2-Azidoethyl)thiophene-2-carboxamide

Product 1

HCID 198091675-(2-Aminoethyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Thienyl)ethyl p-toluenesulphonate (J.A.C.S. 95, 1973, 1247), acetyl chloride and aluminium chloride were reacted in methylene chloride to give 2-[(5-acetyl-2-thienyl)ethyl]p-toluenesulphonate (melting point 111°-112°, from ethanol). This was converted with sodium azide in dimethyl sulphoxide into 5-(2-azidoethyl)-2-thienyl methyl ketone. Oxidation with sodium hypobromite yielded 5-(2-azidoethyl)-2-thiophenecarboxylic acid of melting point 53°-55° C. Treatment of this acid with thionyl chloride gave the corresponding acid chloride which was reacted with ammonia to give 5-(2-azidoethyl)-2-thiophenecarboxamide (melting point 104°-105°, from ethanol). Reaction of this amide with triphenylphosphine and hydrolysis (J. Org. Chem. 40, 1975, 1659) gave 5-(2-aminoethyl)-2-thiophenecarboxamide of melting point 134°-136° (from acetonitrile).

Sources & evidence

ORD record
ord-d3e12e939150495a824acf1e1f8993b0
Source dataset
uspto-grants-1987_03
Patent number
US04652679

Reaction notes

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