Ethyl thiooxamate → HCID 61385373, compound

HRID 1475246Notes

Reaction equation

HRID 1475246 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1)=O.[NH2:16][C:17](=[S:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CCO>[F:13][C:12]([F:15])([F:14])[O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:23][CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 27786912-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-one

Product 1

HCID 61385373HCID 61385373, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(4-(trifluoromethoxy)phenyl)ethanone (20.0 g, 71 mmol) and ethyl 2-amino-2-thioxoacetate (9.466 g, 71 mmol) in absolute EtOH (200 mL) was stirred at 80° C. for 16 h. The mixture was concentrated under reduced pressure, diluted with saturated aqueous sodium carbonate (100 mL) and extracted with EtOAc (4×80 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure, to give the title compound as a white solid (13 g, 57%). MS (ES+) C13H10F3NO3S requires: 317. found: 318 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium carbonate (100 mL)
  3. extractionextracted with EtOAc (4×80 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e2f394fadb74c1abadb53b221576931
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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