N,N-Dimethylaniline → 4-Chloro-8-methylquinazoline

HRID 1358728Notes

Reaction equation

HRID 1358728 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][NH:8][C:7]2=O.O=P(Cl)(Cl)[Cl:15].CN(C)C1C=CC=CC=1.CCCCCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][N:8]=[C:7]2[Cl:15]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 1354713008-Methylquinazolin-4(1H)-one

Product 1

HCID 181856184-Chloro-8-methylquinazoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4 g of 8-methyl 4-quinazolinone, 5 ml POCl3 and 5 ml dimethyl aniline in 40 ml toluene were refluxed 3.5 hours. Workup and trituration with hexane gave 2.6 g of 8-methyl 4 chloro quinazoline, mp-122° C. NMR CDCl3 δ 9.07 (1H, S), 8.12 (1H, d, J=7.7 Hz), 7.8 (1H, d, J=6.0 Hz), 7.60 (1H, t), 2.78 (3H, S).

Sources & evidence

ORD record
ord-f3187c97ffbc40c494accd90541594cd
Source dataset
uspto-grants-2003_07
Patent number
US06596878B2

Reaction notes

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