Sulfuric Acid → HCID 59286657, compound

HRID 1876020Notes

Reaction equation

HRID 1876020 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[S:10][C:9]([NH:11]C(=O)C3C=CC=CC=3)=[N:8][C:5]2=[N:6][CH:7]=1.OS(O)(=O)=O.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[S:10][C:9]([NH2:11])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13481973HCID 13481973, compound

Product 1

HCID 59286657HCID 59286657, compoundYield 63.5%

Procedure

N-(6-Chlorothiazolo[4,5-b]pyridin-2-yl)benzamide (364 mg, 1.256 mmol) in H2SO4 (4 ml, 75 mmol) was heated to 120° C. for 30 minutes, cooled to ambient temperature, basified with 10N NaOH and the resultant solids were collected by filtration to afford 6-chlorothiazolo[4,5-b]pyridin-2-amine (148 mg, 0.797 mmol, 63.5% yield) 1H NMR (500 MHz, DMSO-d6) δ ppm 8.19-8.24 (m, 2H) 8.09 (br. s., 2H).

Workup

  1. filtrationthe resultant solids were collected by filtration

Sources & evidence

ORD record
ord-6cada6d8a7bc4bbea7de4fe9c487a05c
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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