Sulfuryl chloride → 2-Chloro-(1,3)thiazolo(4,5-b)pyridine
Reaction equation
[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]=2Participants
3
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-c212335b49bf4f00963539b646e02c65
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759376B2
Reaction notes
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