Ammonium Hydroxide → HCID 600616, compound

HRID 653612Notes

Reaction equation

HRID 653612 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br.Br[CH2:7][C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O.[OH-].[NH4+]>CO.O>[CH3:2][C:1]1[S:3][CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:4]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723949ThioacetamideHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 600616HCID 600616, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of thioacetamide (5 g) in methanol (25 ml) was added dropwise to a stirred suspension of 3-bromoacetylpyridine hydrobromide (17,75 g) in methanol (89 ml) at room temperature over ten minutes. After about one hour, the hydrobromide of the product crystallized out. The mixture was diluted with ether (100 ml) and the product was isolated by filtration. The solid was dissolved in water and the solution was basified with ammonium hydroxide. The product was extracted into ether and the extract was washed with saturated salt solution, then evaporated to give 2-methyl-4-(pyridin-3-yl)-thiazole as a crystalline solid (8,6 g) Mp 81° C.

Workup

  1. customthe hydrobromide of the product crystallized out
  2. additionThe mixture was diluted with ether (100 ml)
  3. customthe product was isolated by filtration
  4. extractionThe product was extracted into ether
  5. washthe extract was washed with saturated salt solution
  6. customevaporated

Sources & evidence

ORD record
ord-5323d247c1b4488cb2cf422550f2e9aa
Source dataset
uspto-grants-1992_07
Patent number
US05128340

Reaction notes

Loading…