N,N-Dimethylaniline → HCID 19988690, compound

HRID 973573Notes

Reaction equation

HRID 973573 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[NH:18][C:17](=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.P(Cl)(Cl)([Cl:22])=O.CN(C)C1C=CC=CC=1>>[ClH:22].[Cl:22][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:18]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135443938HCID 135443938, compound

Product 1

HCID 19988690HCID 19988690, compoundYield 95.5%

Procedure

2-(2-Methylphenylamino)-4-quinazolone (5.0 g, 0.0198 mol) was dissolved in phosphoryl chloride (20 ml, 0.216 mol) and N,N-dimethylaniline (3.5 ml, 0.025 mol) and refluxed for 3/4 hours. The reaction mixture was poured onto ice/N NaoH (100 ml) and the precipitate washed and dried to give 4-chloro-2-(2-methylphenylamino)quinazoline hydrochloride (5.79 g, 95%), used without purification.

Workup

  1. additionThe reaction mixture was poured onto ice/N NaoH (100 ml)
  2. washthe precipitate washed
  3. customdried

Sources & evidence

ORD record
ord-e09ee0015e7e4765a30d8c83d04f33c2
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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