Bromoacetic Acid → HCID 21298333, compound

HRID 34669Notes

Reaction equation

HRID 34669 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([CH3:7])[N:6]=1.Br[CH2:16][C:17]([OH:19])=[O:18]>CN(C=O)C>[C:17]([CH2:16][S:1][C:2]1[S:3][C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([CH3:7])[N:6]=1)([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6227Bromoacetic AcidHCID 178471202HCID 178471202, compound

Product 1

HCID 21298333HCID 21298333, compoundYield 152.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (8.6 mmol) of ethyl 3-(2-mercapto-4-methyl-1,3-thiazol-5-yl)propionate were initially introduced into 40 ml of dry DMF, and 1.49 g (8.6 mmol) of bromoacetic acid were added. After 2 hours, the solvent was removed in vacuo, and 3.8 g of ethyl 3-[2-(carboxymethylthio)-4-methyl-1,3-thiazol-5-yl]propionate were obtained as an oil. The crude product was taken up in 25 ml of ethanol, 33 ml of 1N sodium hydroxide solution were added, and the reaction mixture was heated at 50° C. After the reaction was complete, the ethanol was removed in vacuo, and the aqueous residue was taken up in concentrated hydrochloric acid at pH 3.0, and the solution was extracted with ethyl acetate. 1.6 g (71%) of the title compound were obtained from the organic phase after drying with MgSO4, evaporation and crystallization with diethyl ether.

Workup

  1. additionwere added
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0a6ab1a84a264ed78f207559ac610c6f
Source dataset
uspto-grants-1988_08
Patent number
US04762848

Reaction notes

Loading…