Dimethylformamide → 2-(2-Ethylsulfanylphenyl)-7-trifluoromethylquinazoline

HRID 521663Notes

Reaction equation

N(OC(C)(C)C)=O.N[C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29][CH2:30][CH3:31])[N:10]=1.CN(C=O)C>O>[CH2:30]([S:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:11]1[N:10]=[CH:9][C:18]2[C:13](=[CH:14][C:15]([C:19]([F:21])([F:22])[F:20])=[CH:16][CH:17]=2)[N:12]=1)[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

324 mg of t-butyl nitrite was added to a mixture of 506 mg of 4-amino-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline and 10 ml of DMF at 100° C., and the mixture was stirred at 100° C. for 45 minutes. Water was added to the cooled reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 74 mg of 2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline (Compound of Present Invention 11).

Workup

extractionthe mixture was extracted with t-butyl methyl ether
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-773220a852194f409f42db985e93e2e9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328121B1

Reaction notes

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