Isopropanol → Isopropyl 2-amino-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate

HRID 2243047Notes

Reaction equation

HRID 2243047 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].[CH:13]([OH:16])([CH3:15])[CH3:14]>>[NH2:9][C:10]1[S:11][C:6]([C:5]([O:16][CH:13]([CH3:15])[CH3:14])=[O:4])=[C:2]([CH2:3][OH:8])[N:12]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 2723790ThioureaHCID 41585753-Chloro-2,4(3H,5H)-furandione

Product 1

HCID 59208427Isopropyl 2-amino-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate

Procedure

A solution of 5 g (37 mmol) of 3-chlorofuran-2,4(3H,5H)-dione and 3.7 g (49 mmol) thiourea in 30 mL isopropanol was heated at refluxed overnight. Solvent was removed and the residue was dissolved in water. The solution was treated with aqueous Na2CO3 precipitating solids. The solids were filtered, washed with water and dried in vacuum. NMR: 1.2 (d, 6H), 4.55 (d, 2H), 4.9 (t, 1H), 5.0 (m, 1H), 7.7 (s, 2H).

Workup

  1. temperatureat refluxed overnight
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in water
  4. additionThe solution was treated with aqueous Na2CO3 precipitating solids
  5. filtrationThe solids were filtered
  6. washwashed with water
  7. customdried in vacuum

Sources & evidence

ORD record
ord-f33d300131ce41879d0a3991f0d17373
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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