N,N-Dimethylethylenediamine → 4-(beta-Dimethylaminoethyl)amino-3-nitrophenyl methyl sulfone

HRID 2291969Notes

Reaction equation

HRID 2291969 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19]>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:19][CH2:18][CH2:17][N:16]([CH3:20])[CH3:15])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 667964-Chloro-3-nitrophenyl methyl sulfone

Product 1

HCID 212775874-(beta-Dimethylaminoethyl)amino-3-nitrophenyl methyl sulfoneYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-3-nitrophenyl methyl sulfone (4 g, 17 mmole) and N,N-dimethylethylenediamine (3.3 g, 37 mmole) in DMSO (20 ml) was stored at 75° C. for 1 hour and poured into crushed ice. The yellow solid precipitate was collected by filtration and was dissolved in ethyl acetate. The organic phase was washed with water-brine mixture twice and brine, dried over sodium sulfate, and evaporated under reduced pressure to give the sulfone (22) (3.8 g, 78%) as a yellow solid. A pure sample (m.p. 130°-131° C.) was obtained by recrystallization from ethyl acetate.

Workup

  1. additionpoured
  2. custominto crushed ice
  3. filtrationThe yellow solid precipitate was collected by filtration
  4. dissolutionwas dissolved in ethyl acetate
  5. washThe organic phase was washed with water-brine mixture twice
  6. dry with materialbrine, dried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-645817e41c254dacb74297f3f75d2b45
Source dataset
uspto-grants-1989_01
Patent number
US04799934

Reaction notes

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