Hydrochloric Acid → 5-Chlorothiazolo[5,4-b]pyridin-2(1H)-one

HRID 1845901Notes

Reaction equation

HRID 1845901 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([O:11]C)=[N:10][C:5]2=[CH:4][CH:3]=1.O1CCOCC1.Cl>O>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 772309095-Chloro-2-methoxy[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 144231285-Chlorothiazolo[5,4-b]pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

To round bottom flask was added give 5-chloro-2-methoxy[1,3]thiazolo[5,4-b]pyridine (1-3) (5.76 g, 28.7 mmol), 1,4-dioxane (90 mL), and a 6N solution of HCl in water (23.9 mL, 144 mmol). The reaction mixture was then heated to 95° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 20 minutes. The crude reaction mixture was then allowed to cool to room temperature, diluted methanol and concentrated to give 5-chloro[1,3]thiazolo[5,4-b]pyridin-2(1H)-one (1-4) as a tan solid. HRMS (M+H)+: observed=186.9731, calculated=186.9727.

Workup

  1. additionTo round bottom flask was added
  2. temperaturecooled
  3. temperaturereflux condenser
  4. customThe crude reaction mixture
  5. temperatureto cool to room temperature
  6. concentrationdiluted methanol and concentrated

Sources & evidence

ORD record
ord-447eba502ec9487a979bd8372ba91c6e
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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