Dimethylformamide → HCID 22030960, compound

HRID 1597247Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[N:9]=[CH:8][NH:7][C:6]2=O.CN(C=O)C.S(Cl)([Cl:29])=O>>[Cl:29][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 1357422856-Methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazolin-4(1H)-one

Product 1

HCID 22030960HCID 22030960, compoundYield 87%

Conditions

Temperature: 60 °C

Procedure

A solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazolin-4-one (930 mg, 3.2 mmol) in thionyl chloride (15 ml) containing DMF (150 μl) was heated at 60° C. for 1.5 hours. The volatiles were removed by evaporation. The residue was dissolved in methylene chloride, the solution was cooled to 5° C. and adjusted to pH8 by the addition of 5% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered and the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with ethyl acetate to give 4-chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (863 mg, 87%).

Workup

customThe volatiles were removed by evaporation
dissolutionThe residue was dissolved in methylene chloride
temperaturethe solution was cooled to 5° C.
additionadjusted to pH8 by the addition of 5% aqueous sodium hydrogen carbonate solution
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
customthe volatiles were removed under vacuum
customThe residue was purified by column chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-6b563befe34843d6b951ef7dab9aa110
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294532B1

Reaction notes

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