Diethyl Ether → Ethyl 2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 258576

Reaction equation

HRID 258576 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:11]([NH2:19])(=[S:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOCC>C(O)C>[C:12]1([C:11]2[S:18][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 575284Ethyl 4-bromo-3-oxobutanoateHCID 683563Thiobenzamide

Product 1

HCID 2797666Ethyl 2-(2-phenyl-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl γ-bromoacetoacetate [2.62 g, 0.9-1.0 mole, described by A. Burger and G. E. Ullyot, J. Org. Chem., 12, 346 (1947)]is added in one portion to a suspension of thiobenzamide [117.5 g, 0.857 mole, described by A. Silberg et al., Ber., 94, 2887 (1961)] in ethanol. The clear solution is refluxed on a steam bath for 2 hr, cooled and slowly added with stirring to ether (3500 ml). The white crystalline precipitate is collected, washed with ether and partitioned between water and ether. Sodium bicarbonate is added in portions until the mixture is alkaline. The mixture is extracted with ether, the ether solution is washed with saturated sodium chloride solution, dried, and evaporated to give ethyl 2-phenylthiazole-4-acetate (VII; R1 = H, R9 = CH2CH3), γmaxCHCl3 1725 cm-1.

Workup

  1. temperatureThe clear solution is refluxed on a steam bath for 2 hr
  2. temperaturecooled
  3. additionslowly added
  4. customThe white crystalline precipitate is collected
  5. washwashed with ether
  6. custompartitioned between water and ether
  7. additionSodium bicarbonate is added in portions until the mixture
  8. extractionThe mixture is extracted with ether
  9. washthe ether solution is washed with saturated sodium chloride solution
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-2964eaeb2c594e1793a3fd1e6a96a762
Source dataset
uspto-grants-1977_07
Patent number
US04033977

Linked notes

Loading…