Hydrochloric Acid → 6-Chlorothiazolo[5,4-b]pyridin-2(1H)-one

HRID 2291577Notes

Reaction equation

HRID 2291577 reaction equation
[NH2:1][C:2]1[C:3]([SH:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10](Cl)(Cl)=[O:11].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:7]=[C:2]2[NH:1][C:10](=[O:11])[S:9][C:3]2=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 178507680HCID 178507680, compound

Product 1

HCID 27475766-Chlorothiazolo[5,4-b]pyridin-2(1H)-oneYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

3-Amino-5-chloro-2-mercaptopyridine (18.8 g) was added to an ice-cooled solution of phosgene (30 g) in toluene (350 ml). 10% Aqueous solution of sodium hydroxide (300 ml) was added dropwise to the stirred mixtured for a period of 1 hour below 20° C. The final mixture was stirred for 1.5 hous at ambient temperature and then stirred for an additional 1 hour at 50° C. After cooling, the aqueous layer was adjusted to pH 4.0 with 4N hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give white powder of 6-chloro-2-oxo-1,2-dihydrothiazolo[5,4-b]pyridine (15.08 g).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-68a86dd277ea4725b52919c9265b3b5f
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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