Phosgene → N-(4,6-dimethylpyrimidin-2-yl)-N-phenylcarbamoyl chloride

HRID 2231628Notes

Reaction equation

HRID 2231628 reaction equation
Cl.[NH:2]([C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17](Cl)([Cl:19])=[O:18]>C1(C)C=CC=CC=1>[CH3:15][C:13]1[CH:12]=[C:11]([CH3:16])[N:10]=[C:9]([N:2]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:17]([Cl:19])=[O:18])[N:14]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 212854452-Anilino-4,6-dimethylpyrimidine hydrochloride

Product 1

HCID 14010626N-(4,6-dimethylpyrimidin-2-yl)-N-phenylcarbamoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Anilino-4,6-dimethylpyrimidine hydrochloride (100 g) was suspended in toluene (1200 ml). A slow stream of phosgene was passed through this over 5.5 hours at 108° (bath temperature of 120°) and then stirred for a further hour at the same temperature. After standing overnight, c. 300 ml of toluene was distilled at a bath temperature of 150°. It was then evaporated under reduced pressure. The oily residue was extracted twice with hexane (1000 ml) and the solution concentrated under reduced pressure. After a period of time crystals formed and these were separated to give N-(4,6-dimethylpyrimidin-2-yl)-N-phenylcarbamoyl chloride. This was shown by thin layer chromatography to be a uniform product, which was used without further purification.

Workup

  1. customover 5.5 hours
  2. customat 108°
  3. custom(bath temperature of 120°)
  4. distillation300 ml of toluene was distilled at a bath temperature of 150°
  5. customIt was then evaporated under reduced pressure
  6. extractionThe oily residue was extracted twice with hexane (1000 ml)
  7. concentrationthe solution concentrated under reduced pressure
  8. customAfter a period of time crystals formed
  9. customthese were separated

Sources & evidence

ORD record
ord-d02783d501b24fec972165df0b4565ea
Source dataset
uspto-grants-1988_11
Patent number
US04783459

Reaction notes

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