Water → 5-chlorothiazolo[5,4-b]pyridin-2-amine

HRID 2366771Notes

Reaction equation

HRID 2366771 reaction equation
[S-:1][C:2]#[N:3].[K+].[Cl:5][C:6]1[N:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.BrBr.O>C(O)(=O)C>[Cl:5][C:6]1[N:11]=[C:10]2[S:1][C:2]([NH2:3])=[N:12][C:9]2=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 793055-Amino-2-chloropyridineHCID 516872Potassium thiocyanate

Product 1

HCID 42660645-chlorothiazolo[5,4-b]pyridin-2-amineYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Potassium thiocyanate (16.0 g, 165 mmol) and 6-chloropyridin-3-amine (2.6 g, 20.2 mmol) were dissolved in acetic acid (52 mL). To this solution was added dropwise a solution of bromine (3.2 mL, 62.5 mmol) in acetic acid (12 mL) under cooling in a water bath, and the mixture was stirred for 2 hr. The mixture was warmed to, stirred for 10 hr, and water (30 mL) was added. This reaction mixture was filtered at 85° C., and the insoluble material was suspended in acetic acid (50 mL) and the suspension was filtered. The obtained filtrate was neutralized with aqueous ammonia solution, and the precipitated solid was collected by filtration and recrystallized from methanol to give the title compound (2.0 g, 54%) as a colorless powder.

Workup

  1. temperatureunder cooling in a water bath
  2. temperatureThe mixture was warmed to,
  3. stirringstirred for 10 hr
  4. filtrationThis reaction mixture was filtered at 85° C.
  5. filtrationthe suspension was filtered
  6. filtrationthe precipitated solid was collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4b3327f9bd8844b8a4a8770265174089
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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