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

HRID 1195514Notes

Reaction equation

HRID 1195514 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-a3ec07bc15a849b1819261be81e1f99f
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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