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

HRID 1800645Notes

Reaction equation

HRID 1800645 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-chloropyridine-3-amine (2.6 g, 20.2 mmol) were dissolved in acetic acid (52 mL). To the 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 allowed to warm to room temperature and stirred for 10 hr, and water (30 mL) was added. The reaction mixture was filtered at 85° C., and the insoluble material was suspended in acetic acid (50 mL) and 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 white crystals.

Workup

  1. temperatureunder cooling in a water bath
  2. stirringstirred for 10 hr
  3. filtrationThe reaction mixture was filtered at 85° C.
  4. filtrationfiltered
  5. filtrationthe precipitated solid was collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8e50f294ef49475db5250ca5f0baaa76
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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