Thionyl Chloride → 5-(6-Bromoquinazolin-4-yl)-thiophen-2-sulfonyl chloride

HRID 1792491Notes

Reaction equation

[Cl:1][S:2]([OH:5])(=O)=[O:3].S(Cl)(Cl)=O.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.C(=O)(O)[O-].[Na+]>O>[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[C:21]1[S:22][C:23]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

14.4 mL chlorosulfonic acid and 14.42 mL thionyl chloride were added to 7.78 g of 6-bromo-4-(2-thienyl)quinazoline (compound in Production Example 96) under ice-cooling in a stream of nitrogen, and the mixture was heated at 60° C. for 16 hours, then poured into iced water, neutralized by adding a sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The residue was recrystallized from ether/hexane, to give 2.47 g of the title compound (pale skin-colored crystals).

Workup

temperaturecooling in a stream of nitrogen
extractionextracted with dichloromethane
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record: ord-2f60f7cf671249b0acf69f03ed62bc04
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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