Ethanol → HCID 21914754, compound

HRID 869395Notes

Reaction equation

HRID 869395 reaction equation
[C:1]([NH:6][C:7]([NH2:9])=[S:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].Br[CH2:11][C:12](=O)[C:13]([OH:15])=[O:14].[CH3:17][CH2:18]O>>[CH2:17]([O:15][C:13]([C:12]1[N:9]=[C:7]([NH:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[S:8][CH:11]=1)=[O:14])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 70684Bromopyruvic AcidHCID 3555130N-Carbamothioyl-2-methylpropanamide

Product 1

HCID 21914754HCID 21914754, compoundYield 100%

Procedure

11A (29.6 g, 0.2 mol) was dissolved in anhydrous EtOH (300 mL). To the solution was added 3-bromo-2-oxo-propionic acid (34 g, 0.17 mol). The mixture was refluxed for 2 hours, then cooled to room temperature, concentrated to dryness, dissolved with ethyl acetate, washed with saturated aqueous of NaHCO3. The organic layer was dried and concentrated to give a crude product 11B (48 g, 100% yield).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated to dryness
  3. dissolutiondissolved with ethyl acetate
  4. washwashed with saturated aqueous of NaHCO3
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1628d8391bd4514b1e333093878dc7f
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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