HCID 59564945, compound → HCID 59564946, compound

HRID 1259326Notes

Reaction equation

HRID 1259326 reaction equation
O=[C:2]([CH3:20])[CH2:3][NH:4][C:5](=[O:19])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[O:7]>S(=O)(=O)(O)O.C(O)(=O)C>[CH3:20][C:2]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:6](=[O:7])[C:5](=[O:19])[NH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59564945HCID 59564945, compound

Product 1

HCID 59564946HCID 59564946, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

N-(2-Oxopropyl)-N′-[3-(trifluoromethyl)phenyl]ethanediamide (1.6 g, 5.5 mmol) and glacial acetic acid (15 ml) were placed in a vial (20 ml). To this solution was added concentrated sulfuric acid (40 drops), and the flask was sealed, and heated with stirring to 100° C. for 90 minutes. Another 40 drops of sulfuric acid was added, and the reaction was allowed to proceed for another 90 minutes. The reaction mixture was allowed to cool, and acetic acid was removed in vacuo. The residue was partitioned between EtOAc (60 ml) and water (40 ml). The aqueous phase was neutralized by addition of NaOH solution to pH 6 to 7. The organic phase was dried, and upon filtration and evaporation a crude product was obtained, which was purified on silica giving 6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrazine-2,3-dione (1.1 g, 74%) as a yellowish solid.

Workup

  1. customthe flask was sealed
  2. temperatureheated
  3. waitto proceed for another 90 minutes
  4. temperatureto cool
  5. customacetic acid was removed in vacuo
  6. customThe residue was partitioned between EtOAc (60 ml) and water (40 ml)
  7. additionThe aqueous phase was neutralized by addition of NaOH solution to pH 6 to 7
  8. customThe organic phase was dried
  9. filtrationupon filtration and evaporation a crude product
  10. customwas obtained
  11. customwhich was purified on silica

Sources & evidence

ORD record
ord-476a9076febf410693b77e9c370dcb33
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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