Ethanol → Ethyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylate

HRID 1948353Notes

Reaction equation

HRID 1948353 reaction equation
Cl[CH:2]1[C:6](=O)[CH2:5][O:4][C:3]1=[O:8].[NH2:9][C:10]([NH2:12])=[S:11].[CH3:13][CH2:14][OH:15]>>[NH2:9][C:10]1[S:11][C:2]([C:3]([O:4][CH2:5][CH3:6])=[O:8])=[C:13]([CH2:14][OH:15])[N:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 41585753-Chloro-2,4(3H,5H)-furandione

Product 1

HCID 12308573Ethyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylate

Procedure

A solution of 5.0 g (37 mmol) of 3-chlorofuran-2,4(3H,5H) -dione and 3.3 g (43 mmol) of thiourea in 50 ml EtOH was heated at reflux for 4 h. Solvent was removed and the residue was dissolved in water with 1N HCl added. The aqueous solution was basified with aqueous Na2CO3. Thick solids that formed were filtered, rinsed with water and dried in vacuo. NMR: 1.2 (t, 3H), 4.2 (q, 2H), 4.6 (s, 2H), 4.9 (s, broad, 1H), 7.8 (s, 2H).

Workup

  1. temperatureat reflux for 4 h
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in water with 1N HCl
  4. additionadded
  5. customThick solids that formed
  6. filtrationwere filtered
  7. washrinsed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2540c8733bbd477f8a7b777adfb078d2
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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