Hydrochloric Acid → [1,3]Thiazolo[5,4-b]pyridin-2-amine

HRID 1959784Notes

Reaction equation

HRID 1959784 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S-:9][C:10]#[N:11].[NH4+].Cl>C(O)C>[N:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:9][C:10]=1[NH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15666Ammonium thiocyanateHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 592050[1,3]Thiazolo[5,4-b]pyridin-2-amineYield 43.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 2-chloro-3-aminopyridine (3 g, 23 mmole), and ammonium thiocyanate (3.5 g, 46.5 mmole) in 23 mL of ethanol was acidified with conc. HCl to pH ˜1 (˜1.8 mL). The reaction mixture was heated to 85° C. for 3 days. At this point, the solvent was evaporated and residual water was removed aziotropically by the distillation of 2-propanol. The yellow residue was mixed with 12 mL of 7 M ammonium hydroxide and 7 mL of chloroform. The solid was isolated by filtration to yield 1.50 g (43%) of the product as a white powder. MS (m/z, ES+): 152 (M+1, 100%).

Workup

  1. customAt this point, the solvent was evaporated
  2. customresidual water was removed aziotropically by the distillation of 2-propanol
  3. additionThe yellow residue was mixed with 12 mL of 7 M ammonium hydroxide and 7 mL of chloroform
  4. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-b2ba1deb59db4e168c7fdb5154ceaf76
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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