Sulfuryl chloride → 2-Chloro-(1,3)thiazolo(4,5-b)pyridine

반응식

[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=S.S(Cl)([Cl:14])(=O)=O>>[Cl:14][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2

참가 물질

반응물 2

HCID 24648Sulfuryl chloride

HCID 21202625[1,3]Thiazolo[4,5-b]pyridine-2-thiol

생성물 1

HCID 513584282-Chloro-(1,3)thiazolo(4,5-b)pyridine수율 40%

실험 절차

The intermediate [1,3]thiazolo[4,5-b]pyridine-2(3H)-thione (644.0 mg, 3.83 mmol, dry powder) was treated with neat sulfuryl chloride (3.08 ml, 38.28 mmol) and allowed to stir at it overnight. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with 1N NaOH, followed by brine, and dried over Na2SO4. Concentration in vacuo gave the title compound (260.0 mg, 40%). LC/MS m/z 171.2 (MH+); retention time 1.55 min. 1H NMR (400 MHz, DMSO-d6) δ 7.58 (m, 1H), 8.62 (d, 1H), 8.78 (d, 1H).

후처리

customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with 1N NaOH
dry with materialdried over Na2SO4
concentrationConcentration in vacuo

출처 및 근거

ORD 기록: ord-c212335b49bf4f00963539b646e02c65
출처 데이터셋: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07759376B2

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