Acetic-formic anhydride → N-(4,6-dimethylpyrimidin-2-yl)-formanilide

HRID 2231629Notes

Reaction equation

HRID 2231629 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OC=O)(=[O:18])C>>[CH3:14][C:12]1[CH:11]=[C:10]([CH3:15])[N:9]=[C:8]([N:1]([CH:16]=[O:18])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:13]=1

Participants

3

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 91650Pyrimethanil

Product 1

HCID 14327563N-(4,6-dimethylpyrimidin-2-yl)-formanilide

Procedure

2-Anilino-4,6-dimethylpyrimidine (10 g) was added to formic-acetic anhydride (prepared from formic acid (5 ml) and acetic anydride (12 ml)) and the mixture heated gently to 40° to give a clear solution. After standing for 4 days, a crystalline solid separated and toluene was added to give a clear solution again. The mixture was evaporated to dryness, more toluene added and reevaporated. The product was recrystallised from ethyl acetate/light petroleum to give N-(4,6-dimethylpyrimidin-2-yl)-formanilide, m.p. 134°-5°. (Compound 3).

Workup

  1. temperaturethe mixture heated gently to 40°
  2. customto give a clear solution
  3. customa crystalline solid separated
  4. additiontoluene was added
  5. customto give a clear solution again
  6. customThe mixture was evaporated to dryness, more toluene
  7. additionadded
  8. customreevaporated
  9. customThe product was recrystallised from ethyl acetate/light petroleum

Sources & evidence

ORD record
ord-e3918f7c53824b01b596dc4d8f4dfbd6
Source dataset
uspto-grants-1988_11
Patent number
US04783459

Reaction notes

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