Ammonium Hydroxide → N-octanesulfonylacetamide

HRID 132085Notes

Reaction equation

HRID 132085 reaction equation
[CH2:1]([S:9]([CH2:12][C:13]([O:15]C)=O)(=[O:11])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[NH4+:18]>CO>[CH2:1]([S:9]([CH2:12][C:13]([NH2:18])=[O:15])(=[O:11])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 479449Methyl 2-octylsulfonylacetate

Product 1

HCID 479435N-octanesulfonylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl n-octanesulphonylacetate (35 g, 0.143 mole) in 350 ml of anhydrous methanol was stirred magnetically at room temperature. To this solution was added 24 ml of aqueous ammonium hydroxide (27%, 6.48 g, 0.185 mole) in drops over a period of 30 minutes. The solution was stirred for 24 h and the white precipitate formed was filtered. The solid was recrystallized from hot ethyl acetate to obtain the required acetamide III-50 as a crystalline solid, mp. 140-142° C., 33 g, 97.6%.

Workup

  1. customthe white precipitate formed
  2. filtrationwas filtered
  3. customThe solid was recrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-e3307898b4a94381a9c376ec7284c3c5
Source dataset
uspto-grants-2008_06
Patent number
US07385086B2

Reaction notes

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