N,N-Dimethylethylenediamine → N-[2-(Dimethylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide

HRID 463681Notes

Reaction equation

HRID 463681 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19]>C1COCC1>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH:19][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 117911194-[(Methylsulfonyl)amino]benzoyl chloride

Product 1

HCID 17639298N-[2-(Dimethylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a three-neck flask equipped with mechanical stirrer, cooled in ice bath under nitrogen atmosphere, place a solution of 4.67 g (0.02 mole) of 4-[(methylsulfonyl)amino]benzoyl chloride in 30 ml of anhydrous THF. Add dropwise a solution of 1.77 g (0.02 mole) of N,N-dimethylethylenediamine in 10 ml of anhydrous THF; white solid precipitate forms immediately. Stir the mixture at ice temperature for one-half hour and at room temperature for one-half hour. Collect the solid by filtration, wash with dichloromethane, and recrystallize from methanol ether mixture to provide the title compound.

Workup

  1. customIn a three-neck flask equipped with mechanical stirrer
  2. temperaturecooled in ice bath under nitrogen atmosphere
  3. waitat room temperature for one-half hour
  4. customCollect the solid
  5. filtrationby filtration
  6. washwash with dichloromethane
  7. customrecrystallize from methanol ether mixture

Sources & evidence

ORD record
ord-64e7cfdaf7b94818889bd1e440f700a1
Source dataset
uspto-grants-1985_10
Patent number
US04544654

Reaction notes

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