Thiourea → Methyl 4-acetyl-2-amino-1,3-thiazole-5-carboxylate

HRID 1948361Notes

Reaction equation

HRID 1948361 reaction equation
Cl[CH:2]([C:7](=O)[C:8]([O:12]C)(OC)[CH3:9])[C:3]([O:5][CH3:6])=[O:4].[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[C:8]([C:7]1[N:15]=[C:16]([NH2:18])[S:17][C:2]=1[C:3]([O:5][CH3:6])=[O:4])(=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 59208484Methyl 2-chloro-4,4-dimethoxy-3-oxopentanoate2×

Product 1

HCID 59208430Methyl 4-acetyl-2-amino-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.37 g (19 mmol) methyl 2-chloro-4,4-dimethoxy-3-oxopentanoate (Intermediate 221) and 1.8 g (24 mmol) thiourea in 50 ml EtOH was heated at reflux for 3 h. Solvent was removed and the residue was dissolved in 1:1 acetone-5N HCl and the solution was heated at reflux for 4 h. Acetone was removed and the aqueous residue was neutralized with 50% NaOH and then basified with aqueous Na2CO3. Precipitated solids were filtered, washed with water and dried in vacuo. NMR (d6-DMSO): 2.4 (s, 3H), 3.7 (s, 3H), 8.0 (s, 2H).

Workup

  1. temperatureat reflux for 3 h
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in 1:1 acetone-5N HCl
  4. temperaturethe solution was heated
  5. temperatureat reflux for 4 h
  6. customAcetone was removed
  7. customPrecipitated solids
  8. filtrationwere filtered
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-529780feedfb4a36862f2db59d456f18
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…