Sodium Iodide → N-(2-dimethylamino-ethyl)-N-methylsulphonyl-4-nitroaniline

HRID 898532Notes

Reaction equation

HRID 898532 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.O>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][N:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 5238Sodium Iodide2×HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 11430Potassium Carbonate2×HCID 4689022N-(4-nitrophenyl)methanesulfonamide

Product 1

HCID 22668565N-(2-dimethylamino-ethyl)-N-methylsulphonyl-4-nitroaniline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

36.00 g (0.166 mol) of N-(4-nitro-phenyl)-methanesulphonic acid amide was dissolved in 2000 mL acetone. The solution was combined with 47.8 g (0.332 mol) of 1-chloro-2-dimethylaminoethane * HCl, 68.8 g (0.498 mol) of potassium carbonate, 5.0 g (0.033 mol) of sodium iodide and 50 mL water. It was refluxed for 16 hours with stirring. After the addition of another 23.9 g (0.166 mol) of 1-chloro-2-dimethylaminoethane * HCl, 45.9 g (0.332 mol) of potassium carbonate and 5.0 g (0.033 mol) of sodiumiodide, the mixture was refluxed for 5 hours with stirring. At RT the inorganic salts were filtered off. The filtrate was evaporated down i. vac. and the residue dissolved in EtOAc. The org. phase was washed 2× with semisat. aqueous sodium chloride solution, dried over magnesium sulphate, filtered and evaporated down i. vac.

Workup

  1. temperatureIt was refluxed for 16 hours
  2. temperaturethe mixture was refluxed for 5 hours
  3. stirringwith stirring
  4. filtrationAt RT the inorganic salts were filtered off
  5. customThe filtrate was evaporated down i
  6. dissolutionand the residue dissolved in EtOAc
  7. washphase was washed 2× with semisat
  8. dry with materialaqueous sodium chloride solution, dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated down i

Sources & evidence

ORD record
ord-bae87997aa0f4d0b82ece6982e347cc6
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

Loading…