N,N-Dimethylaniline → HCID 17954508, compound

HRID 1766097Notes

Reaction equation

HRID 1766097 reaction equation
O=P(Cl)(Cl)[Cl:3].[C:6]([C:8]1[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)=[N:10][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:12][C:13]=1O)#[N:7].CN(C)C1C=CC=CC=1>O1CCOCC1>[Cl:3][C:13]1[N:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:8]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178510523HCID 178510523, compound

Product 1

HCID 17954508HCID 17954508, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

POCl3 (50 ml) was added to a stirred solution of 5-cyano-4-(3-nitrophenyl)-2-phenyl-6-hydroxy-pyrimidine (example 31(a), 15.0 g) and dimethylaniline (0.5 ml) in dry 1,4-dioxane p.a. (200 ml). After 3 h at 90° C., the warm mixture was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane and ice water was added. The resulting precipitate was filtered off and washed with water. Residual water was removed by coevaporation with 1,4-dioxane.

Workup

  1. filtrationthe warm mixture was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1,4-dioxane
  4. additionice water was added
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water
  7. customResidual water was removed by coevaporation with 1,4-dioxane

Sources & evidence

ORD record
ord-d2867b85fdbc4a0abc5c9b4cc6282da4
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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