Ammonia → HCID 67055903, compound

HRID 2036842Notes

Reaction equation

HRID 2036842 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9][CH2:10][C:11]([O:13]C)=O)[CH:5]=[N:6][CH:7]=1.[NH3:15]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9][CH2:10][C:11]([NH2:15])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 67055984Methyl 2-((5-bromopyridin-3-yl)methylthio)acetate

Product 1

HCID 67055903HCID 67055903, compoundYield 72%

Procedure

A solution of methyl 2-((5-bromopyridin-3-yl)methylthio)acetate (1.2 g, 4.5 mmol) in NH3 (2.0 M in MeOH, 40 mL) was heated at 80° C. in a sealed vessel for 2 h. After this time, the reaction mixture was allowed to cool to room temperature and then the solvent was evaporated under reduced pressure. The resulting residue was recrystallized from EtOAc/hexanes to provide 2-((5-bromopyridin-3-yl)methylthio)acetamide (0.8 g, 72% yield). LCMS Method W: retention time 1.08 min; [M+1]=263.0.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe resulting residue was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-22c26c2f30dc461fb5d9c43e80e4ecd6
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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