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

HRID 1648255Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[Cl:24][CH2:25][C:26]#[N:27].[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:24][CH2:25][C:26]1[N:27]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (8.0 g) and chloroacetonitrile (25 ml), powdered aluminum chloride (6.7 g) was added, followed by stirring at 100° C. for 2 hours. The reaction mixture was poured over water and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (10:1, v/v) to yield 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.9 g, 52%), which was then recrystallized from acetone to yield a colorless prismatic crystal having a melting point of 183° to 184° C.

Workup

additionwas added
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried (MgSO4)
distillationafter which the solvent was distilled off
washeluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record: ord-c7268d8b012640f583c438c848d6fabb
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436247

Reaction notes

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