Ethanolamine → N-(2-hydroxyethyl)-4-thiazolecarboxamide

HRID 1085495Notes

Reaction equation

HRID 1085495 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([O:8]CC)=O)[N:3]=[CH:2]1.[CH2:11]([CH2:13][NH2:14])[OH:12]>>[OH:12][CH2:11][CH2:13][NH:14][C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)=[O:8]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 5003096Ethyl thiazole-4-carboxylate

Product 1

HCID 20060259N-(2-hydroxyethyl)-4-thiazolecarboxamide

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-thiazolecarboxylate (24.49 g) and monoethanolamine (28.0 ml) was heated at 100° C. with stirring for 1 hour 20 minutes. After being cooled, the mixture was subjected to column chromatography on silica gel (245 g) and eluted with chloroform. The fractions containing the objective compound were combined and concentrated under reduced pressure to give a light brown oil of N-(2-hydroxyethyl)-4-thiazolecarboxamide (25.93 g).

Workup

  1. temperatureAfter being cooled
  2. washeluted with chloroform
  3. additionThe fractions containing the objective compound
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2464eafe9acc4eecac2f722931d9bdd3
Source dataset
uspto-grants-1991_04
Patent number
US05010093

Reaction notes

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