Ethyl bromopyruvate → HCID 4067950, compound

HRID 1073686Notes

Reaction equation

HRID 1073686 reaction equation
[C:1]([NH:9][C:10]([NH2:12])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:19]([O:18][C:16]([C:15]1[N:12]=[C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:11][CH:14]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2735473Benzoylthiourea

Product 1

HCID 4067950HCID 4067950, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 19.02 g. of benzoylthiourea and 19.12 g. of ethyl bromopyruvate in 300 ml. of ethanol was refluxed for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (1 liter) and 20% aqueous sodium carbonate (400 ml.). The organic layer was separated, washed successively with 20% aqueous sodium carbonate (3×400 ml.), water (2×400 ml.) and a brine solution (2×400 ml.) and dried over sodium sulfate. The solution was concentrated to about 50 ml. and the precipitated solids filtered and dried, 20.16 g., m.p. 146-147° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (1 liter) and 20% aqueous sodium carbonate (400 ml.)
  3. customThe organic layer was separated
  4. washwashed successively with 20% aqueous sodium carbonate (3×400 ml.), water (2×400 ml.)
  5. dry with materiala brine solution (2×400 ml.) and dried over sodium sulfate
  6. concentrationThe solution was concentrated to about 50 ml
  7. filtrationand the precipitated solids filtered
  8. customdried

Sources & evidence

ORD record
ord-fcec0f3c88934af88258ecc1d6332898
Source dataset
uspto-grants-1990_11
Patent number
US04970318

Reaction notes

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