Water → 1357247-55-2

HRID 709411Notes

Reaction equation

HRID 709411 reaction equation
Br[CH2:2][C:3](=O)[C:4]([OH:6])=[O:5].[NH2:8][C:9](=[S:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH2:13]([O:12][C:10]([C:9]1[S:15][C:3]([C:4]([OH:6])=[O:5])=[CH:2][N:8]=1)=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 70684Bromopyruvic AcidHCID 516892Sodium BicarbonateHCID 2733398Ethyl thiooxamate2×

Product 1

HCID 667149791357247-55-2Yield 47.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Bromopyruvic acid (22.7 g, 135.33 mmol) was added to a solution of ethyl 2-amino-2-thioxoacetate (Intermediate W, 18 g, 135.3 mmol) in dioxane (200 mL) and refluxed for 5 h. After completion the reaction mixture was poured into water (200 mL), the residue was basified with sat NaHCO3 and extracted with EtOAc (2×250 mL). The aqueous layer was acidified with 2N HCl and extracted with EtOAc (2×250 mL) The combined extracts were washed with water (250 mL), brine (250 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford 2-(ethoxycarbonyl)thiazole-5-carboxylic acid (13 g crude). The crude was carried to next step without further purification.

Workup

  1. temperaturerefluxed for 5 h
  2. extractionextracted with EtOAc (2×250 mL)
  3. extractionextracted with EtOAc (2×250 mL) The combined extracts
  4. washwere washed with water (250 mL), brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4ccbbc57444841cdb71081687cb8fe7f
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

Loading…