Hydrochloric Acid → HCID 9837336, compound

HRID 1279238Notes

Reaction equation

HRID 1279238 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[SH:10].[OH-].[Na+].Cl[CH:14]([F:16])[F:15].Cl>O1CCOCC1.O>[F:15][CH:14]([F:16])[S:10][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 178527821HCID 178527821, compound

Product 1

HCID 9837336HCID 9837336, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of thiazolo[4,5-b]pyridine-2-thiol (2.0 g, 12 mmol) in dioxane is treated with a solution of sodium hydroxide (4.8 g, 120 mmol) in water, heated to 70° C., treated with a steady stream of chlorodifluoromethane for 75 minutes, and poured onto ice. The resultant aqueous mixture is acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic extract is dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and several ethyl acetate/hexanes solutions gives the title product as a light yellow solid (0.86 g, 33% yield, mp 41-43° C.).

Workup

  1. additionpoured onto ice
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialis dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-ad89528a75534f169e706b67bd174011
Source dataset
uspto-grants-2002_09
Patent number
US06448262B1

Reaction notes

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