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

HRID 2356837Notes

Reaction equation

HRID 2356837 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]=2

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21202625[1,3]Thiazolo[4,5-b]pyridine-2(3H)-thione

Product 1

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

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

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

Sources & evidence

ORD record
ord-c212335b49bf4f00963539b646e02c65
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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