ethyl 3-amino-3-thioxopropanoate → HCID 19790104, compound

HRID 1381403Notes

Reaction equation

HRID 1381403 reaction equation
[NH2:1][C:2](=[S:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(OCC)C>[C:4]([C:3]1[N:1]=[C:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[S:9][CH:2]=1)([OH:6])=[O:5]

Participants

3

Reactant 1

HCID 2771567ethyl 3-amino-3-thioxopropanoate

Product 1

HCID 19790104HCID 19790104, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-amino-3-thioxopropionate (73.5 g) in diethyl ether (100 ml) was added to a solution of bromopiruvic acid (88.5 g) in diethyl ether (300 ml) and stirred for 15 hours at ambient temperature. The precipitates were collected by filtration and added to a mixture of water (500 ml) and diethyl ether (300 ml) and then adjusted to pH 7.5 with 20% aqueous sodium carbonate. The separated aqueous solution was adjusted to pH 1.0 with conc. hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was dried over magnesium sulfate and evaporated. The residue was washed with diisopropyl ether to give ethyl 2-(4-carboxythiazol-2-yl)acetate (57.1 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. additionadded to a mixture of water (500 ml) and diethyl ether (300 ml)
  3. extractionextracted with diethyl ether
  4. dry with materialThe diethyl ether layer was dried over magnesium sulfate
  5. customevaporated
  6. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-a136357439c940ce85752d9140a4a941
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

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