Acetic Anhydride → HCID 59139820, compound

HRID 1799469Notes

Reaction equation

HRID 1799469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C1COCC1>[O:14]=[C:13]1[NH:12][C:11](=[O:15])[CH:10]=[N:9][N:8]1[C:4]1[CH:3]=[C:2]([NH:1][C:16](=[O:18])[CH3:17])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68701770HCID 68701770, compound

Product 1

HCID 59139820HCID 59139820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-(3-aminophenyl)-1,2,4-triazine-3,5(2H,4H)-dione (1.2 g, 5.88 mmol) in THF (20 mL) was added acetic anhydride (1.2 g, 11.8 mmol) and the mixture was heated at 50° C. After 2 h the mixture was cooled at room temperature, quenched with water and extracted with ethyl acetate (×3).The organic layers were washed with brine, dried over MgSO4, filtered and concentrated to afford the 900 mg, 62% yield, of N-(3-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 9(D) (900 mg, 62%) which is used in next step without any further purification.

Workup

  1. temperatureAfter 2 h the mixture was cooled at room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate (×3).The organic layers
  4. washwere washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the 900 mg, 62% yield
  9. customof N-(3-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 9(D) (900 mg, 62%) which is used in next step without any further purification

Sources & evidence

ORD record
ord-345c31b02b8f43079c4f2c0d6bb67188
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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