Acetone → (3,4-Dichlorophenyl)methanesulfonamide

HRID 1663608Notes

Reaction equation

HRID 1663608 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][S:10](Cl)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)=O.[OH-].[NH4+:19]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][S:10]([NH2:19])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14923Ammonium HydroxideHCID 2794622(3,4-Dichlorophenyl)methanesulfonyl chloride

Product 1

HCID 20472420(3,4-Dichlorophenyl)methanesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of (3,4-dichloro-phenyl)-methanesulfonyl chloride (500 g, 1.93 mol) and acetone (470 mL) was added over 2 h to cooled (0-5° C.), stirred concentrated ammonium hydroxide (28%, 900 mL, 227 g NH3, 13.3 mol). The reaction mixture was maintained below 12° C. during the addition. The reaction mixture was allowed to warm to room temperature and was stirred for 1 h. Water (900 mL) was added to the reaction mixture and it was stirred for 1 h. The white solid was collected by filtration, washed with cold water (2×500 mL), and vacuum dried to give 375 g (81%) of (3,4-dichloro-phenyl)-methanesulfonamide with 99% purity (as determined by HPLC).

Workup

  1. temperatureThe reaction mixture was maintained below 12° C. during the addition
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 1 h
  4. filtrationThe white solid was collected by filtration
  5. washwashed with cold water (2×500 mL), and vacuum
  6. customdried

Sources & evidence

ORD record
ord-651d062b4ad345d8bcbd8621d0d3ff25
Source dataset
uspto-grants-2011_10
Patent number
US08034960B2

Reaction notes

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