Ethanol → Ethyl 2-aminothiazole-4-carboxylate

HRID 488455Notes

Reaction equation

HRID 488455 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:16][CH3:17])=[O:9])[N:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 162177172-Amino-4-thiazolecarboxylic acid hydrobromide

Product 1

HCID 73216Ethyl 2-aminothiazole-4-carboxylate

Procedure

2-Aminothiazole-4-carboxylic acid hydrobromide (10 g) (E. C. Roberts and Y. F. Shealy, J. Med. Chem. 15 (1972)1310-1312) in ethanol (35 ml) was treated with conc. sulfuric acid and refluxed for 48 hours. The solution was evaporated to 25% of original volume and water (20 ml) added. It was made basic by addition of NaHCO3, the solid filtered, washed with water and dried under vacuum to give the title compound (5.64 g). NMR δ(CDCl3) 137 (3H,t), 4.36(2H,q), 5.39(2H, broad), 7.43(1H,s).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solution was evaporated to 25% of original volume and water (20 ml)
  3. additionadded
  4. additionIt was made basic by addition of NaHCO3
  5. filtrationthe solid filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-23bd6fa5e3a04a75ae0f91c805aa3888
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Reaction notes

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