Chloroacetonitrile → 2-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

HRID 266119Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[Cl:28][CH2:29][C:30]#[N:31]>O>[Cl:28][CH2:29][C:30]1[N:31]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[C:7]2[C:6](=[CH:23][C:22]([O:24][CH3:25])=[C:21]([O:26][CH3:27])[CH:20]=2)[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Aluminium chloride powder (6.7 g) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (8.0 g) and chloroacetonitrile (25 ml), and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (10:1, v/v) gave 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (4.9 g, 52%). This compound was recrystallized from acetone. Colorless prisms, mp. 183°-184° C.

Workup

extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
washThe fractions eluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record: ord-f78c4572e2e544389c4549ad0dfb595f
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650410

Reaction notes

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