N,N-Dimethylaniline → HCID 86673510, compound

HRID 629028Notes

Reaction equation

HRID 629028 reaction equation
CN(C)C1C=CC=CC=1.[CH3:10][O:11][C:12]1[C:13](=O)[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[N:16][CH:17]=1.O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:13]1[C:12]([O:11][CH3:10])=[CH:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[N:14]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 67295363HCID 67295363, compound

Product 1

HCID 86673510HCID 86673510, compoundYield 61%

Procedure

In ice bath, dimethyl-phenyl-amine (1.19 mL, 1.0 eq) was added dropwise to a slurry of 5-Methoxy-2-(4-nitro-phenyl)-3H-pyrimidin-4-one (2.3 g, 1.0 eq) in POCl3 (4.4 mL, 5.0 eq) and the mixture was refluxed overnight. Excess POCl3 was evaporated in vacuo and the residue was poured into ice-water. After formation of precipitates, the mixture was filtered and the residue was dried solid in vacuo. A product was obtained as a white solid (2.47 g, 61%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customExcess POCl3 was evaporated in vacuo
  3. additionthe residue was poured into ice-water
  4. customAfter formation of precipitates
  5. filtrationthe mixture was filtered
  6. customthe residue was dried solid in vacuo

Sources & evidence

ORD record
ord-35873e3cafcc4af9816c59e54149140e
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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