Thiourea → Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylate

HRID 1660568Notes

Reaction equation

HRID 1660568 reaction equation
Cl[CH:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[NH2:15][C:13]1[S:14][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH:9]([CH3:11])[CH3:10])[N:12]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 20557029Ethyl 2-chloro-4-methylpentanoate

Product 1

HCID 824436Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylateYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Utilizing the procedure of Example 1, a mixture of 1.97 g (0.01 mol) of ethyl 2-chloro-4-methyl-pentanoate, 0.76 g (0.01 mol) of thiourea and 30 ml of ethanol was held at reflux for 18 hours. Ethanol was removed under reduced pressure. The residue was crystallized from hexane. The solid precipitates were dissolved in ether. The ether solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from benzene-ether to give 0.85 g (39.6%) of ethyl 2-amino-4-isopropyl-5-thiazolecarboxylate, m.p. 173°-176° C.

Workup

  1. temperatureat reflux for 18 hours
  2. customEthanol was removed under reduced pressure
  3. customThe residue was crystallized from hexane
  4. customThe solid precipitates
  5. dissolutionwere dissolved in ether
  6. washThe ether solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from benzene-ether

Sources & evidence

ORD record
ord-031f732e532d47bab1a6100ae48e1a54
Source dataset
uspto-grants-1981_12
Patent number
US04308391

Reaction notes

Loading…