Acetone → (2,6-Dimethylphenyl)methanesulfonamide

HRID 1177670Notes

Reaction equation

HRID 1177670 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][S:10](Cl)(=[O:12])=[O:11].CC(C)=O.[OH-].[NH4+:19]>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][S:10]([NH2:19])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14923Ammonium HydroxideHCID 11218255(2,6-dimethylphenyl)methanesulfonyl Chloride

Product 1

HCID 23161120(2,6-Dimethylphenyl)methanesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of (2,6-dimethylphenyl)-methanesulfonyl chloride (452 g, 2.07 mol) and acetone (2.0 L) was added over 90 m to cooled (0-5° C.), stirred, concentrated ammonium hydroxide (28%, 900 mL, 227 g NH3, 13.3 mol). The reaction mixture was maintained <10° C. during the addition. The reaction mixture was allowed to warm to room temperature and was stirred for 1 h. Water (2.0 L) was added to the reaction mixture and it was stirred for 1 h at 0-5° C. The white solid was collected by filtration, washed with cold water (2×1 L), and vacuum dried to give 349 g (85%) of (2,6-dimethylphenyl)-methanesulfonamide with 99% purity (as determined by HPLC).

Workup

  1. temperatureThe reaction mixture was maintained <10° C. during the addition
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 1 h
  4. stirringwas stirred for 1 h at 0-5° C
  5. filtrationThe white solid was collected by filtration
  6. washwashed with cold water (2×1 L), and vacuum
  7. customdried

Sources & evidence

ORD record
ord-8504d912a10544828f67fa32fdc00e3a
Source dataset
uspto-grants-2010_11
Patent number
US07842837B2

Reaction notes

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