2-Aminopyridine → HCID 20228692, compound

HRID 1731327Notes

Reaction equation

HRID 1731327 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1)=O.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C(O)C>[N:15]1[C:3]([C:5]2[CH:6]=[CH:7][C:8]3[S:12][C:11](=[O:13])[NH:10][C:9]=3[CH:14]=2)=[CH:2][N:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=12

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 15054199HCID 15054199, compound

Product 1

HCID 20228692HCID 20228692, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-bromoacetyl-2-benzothiazolinone (3.3 g) and 2-aminopyridine (4.2 g) in ethanol was refluxed for 5 hours and the reaction mixture was evaporated in vacuo. To the residue was added a mixture of water and ethyl acetate and the resulting mixture was acidified to pH 1.0 with 10 % hydrochloric acid. The precipitate was collected by filtration and added to a solution of saturated aqueous sodium bicarbonate. The mixture was stirred for 30 minutes. The precipitate was collected by filtration, washed with water and recrystallized from aqueous ethanol to give 5-(imidazo[1,2-a]pyridin-2-yl)-2-benzothiazolinone (0.24 g). mp>270° C.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of water and ethyl acetate
  4. filtrationThe precipitate was collected by filtration
  5. additionadded to a solution of saturated aqueous sodium bicarbonate
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-1554fd4a7c4f40a1975bf7da255d4b5e
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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