Ethanol → Ethyl alpha-acetamido-2-acetamidothiazol-4-ylacetate

HRID 1395402Notes

Reaction equation

HRID 1395402 reaction equation
[C:1]([NH:4][CH:5]([C:11](=O)[CH2:12]Br)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C(O)C.CCOCC.[C:23]([NH:26][C:27]([NH2:29])=[S:28])(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:1]([NH:4][CH:5]([C:11]1[N:29]=[C:27]([NH:26][C:23](=[O:25])[CH3:24])[S:28][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 2723593AcetylthioureaHCID 15137540Ethyl 2-acetamido-4-bromo-3-oxobutanoate

Product 1

HCID 12763195Ethyl alpha-acetamido-2-acetamidothiazol-4-ylacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 34.6 g. of ethyl α-acetamido-β-oxo-γ-bromobutyrate in a mixture of 50 ml. of ethanol and 20 ml. of ether are added 18.9 g. of N-acetylthiourea and 15 ml. of pyridine. The mixture is heated under reflux for 4 hours, and condensed under reduced pressure. The condensate is extracted with ethyl acetate and the extract is washed with 5% aq. NaHCO3, then with water, and dried. The oily substance which is obtained from the extract by removal of the solvent is purified by silica gel chromatography to give ethyl α-acetamido-2-acetamidothiazol-4-ylacetate. 4.46 g. Melting point: 148.9°-150° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customcondensed under reduced pressure
  4. extractionThe condensate is extracted with ethyl acetate
  5. washthe extract is washed with 5% aq. NaHCO3
  6. dry with materialwith water, and dried
  7. customThe oily substance which is obtained from the
  8. extractionextract by removal of the solvent
  9. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-f9d1b18848794ff0abe4c23c72de00a8
Source dataset
uspto-grants-1980_05
Patent number
US04203899

Reaction notes

Loading…