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

反応式

[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

参加物

反応物 2

HCID 24648Sulfuryl chloride

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-c212335b49bf4f00963539b646e02c65
出典データセット: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07759376B2

反応ノート

読み込み中…

参加物