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

HRID 1792490노트

반응식

HRID 1792490 반응식
[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>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

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 220314806-Bromo-4-(2-thienyl)quinazoline

생성물 1

HCID 220314245-(6-Bromoquinazolin-4-yl)-thiophen-2-sulfonyl chloride

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

0.18 mL chlorosulfonic acid and 0.19 mL thionyl chloride were added to 0.1 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 for 13 hours at 60° C., then neutralized by adding water and a sodium bicarbonate solution and extracted with dichloromethane. 5-(6-Bromoquinazolin-4-yl)-thiophen-2-sulfonyl chloride obtained by drying the organic layer over anhydrous sodium sulfate was dissolved in 3 mL tetrahydrofuran, then 0.3 mL morpholine was added thereto, and the mixture was stirred at room temperature for 1 hour. The solvent was removed, and the positional isomers were separated and purified by silica gel column chromatography (ethyl acetate/hexane) to give 57 mg of the title compound (colorless crystals).

후처리

  1. temperaturecooling in a stream of nitrogen
  2. extractiona sodium bicarbonate solution and extracted with dichloromethane

출처 및 근거

ORD 기록
ord-2459a44217094dd5933f672c4625039f
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074801B1

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