Ethylamine → 2-chloro-N-ethyl-4-thiazolecarboxamide

HRID 1939042Notes

Reaction equation

HRID 1939042 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7](Cl)=[O:8])[N:6]=1.ClC1S[CH:13]=[C:14](C(O)=O)[N:15]=1.S(Cl)(Cl)=O.C(N)C>O.CN(C=O)C>[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:15][CH2:14][CH3:13])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 24386Thionyl ChlorideHCID 218030262-Chloro-1,3-thiazole-4-carboxylic acidHCID 450815362-Chloro-1,3-thiazole-4-carbonyl chloride

Product 1

HCID 186300282-chloro-N-ethyl-4-thiazolecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-thiazolecarboxylic acid chloride (prepared from 2-chloro-4-thiazolecarboxylic acid, thionyl chloride and a catalytic amount of DMF) was reacted with 70% ethylamine in water to yield 2-chloro-N-ethyl-4-thiazolecarboxamide. This compound was reacted with TMSCl using the method of step c of Example 248. Purification by flash chromatography with 3% ethyl acetate-hexane gave 2.5 g of the title compound as a light yellow oil in 55.6% yield. nD26 1.5313.

Sources & evidence

ORD record
ord-a6e5b44223c5486b830906a0896dcf54
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

Loading…