Dimethylformamide → 4-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazoline

HRID 1421058Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]3)=[CH:11][C:10]=2[O:20][CH3:21])[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)([Cl:24])=O.CN(C=O)C>C1(C)C=CC=CC=1>[Cl:24][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (412 mg, 1.44 mmol), thionyl chloride (5 ml) and DMF (0.2 ml) was heated at reflux for 1 hour. The mixture was diluted with toluene and the volatiles were removed by evaporation. The residue was suspended in methylene chloride, cooled to 0° C. and aqueous sodium hydrogen carbonate solution was added. The resulting precipitate was collected by filtration and dried under vacuum to give 4-chloro-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (258 mg, 59%).

Workup

temperaturewas heated
temperatureat reflux for 1 hour
customthe volatiles were removed by evaporation
additionaqueous sodium hydrogen carbonate solution was added
filtrationThe resulting precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-7c71440f44bb45dfb8aac60c3a033a34
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071921

Reaction notes

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