Dimethylamine → N,N-Dimethylbenzenesulfonamide

HRID 2224370Notes

Reaction equation

HRID 2224370 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][NH:12][CH3:13]>C1COCC1.O>[CH3:11][N:12]([CH3:13])[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 84423N,N-DimethylbenzenesulfonamideYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenylsulfonyl chloride (10 mL, 78 mmol) in THF (50 mL) was cooled to 0° C. and treated dropwise with dimethylamine (20 mL) as a 40% solution in water maintaining a temperature below 50° C. The reaction was warmed to room temperature for one hour and poured into water. The solution was concentrated to remove THF and the residue was cooled to 0° C. The resulting solid was filtered and dried in vacuo to afford 83A (14 g, 97%).

Workup

  1. concentrationThe solution was concentrated
  2. customto remove THF
  3. temperaturethe residue was cooled to 0° C
  4. filtrationThe resulting solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a061b6f8f784428e96a83a22e388c41d
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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