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

HRID 1007391Notes

Reaction equation

HRID 1007391 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].Cl[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:7]=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 5238Sodium Iodide3×HCID 79012-Chloro-N,N-dimethylethylamine3×HCID 11430Potassium Carbonate3×HCID 4689022N-(4-nitrophenyl)methanesulfonamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Conditions

Temperature
50 °C

Procedure

38.9 g of N-methylsulphonyl-4-nitroaniline are dissolved in 2.0 l of acetone, 51.9 g of 1-chloro-2-dimethylamino-ethane, 77.4 g of potassium carbonate and 5.0 g of sodium iodide added and the mixture is stirred for a total of 4 days at 50° C., adding, after 12 hours, a further 25.9 g of 1-chloro-2-dimethylamino-ethane, 49.8 g of potassium carbonate and 5.0 g of sodium iodide in 500 ml of acetone and, after 36 hours, a further 26.0 g of 1-chloro-2-dimethylamino-ethane, 50.0 g of potassium carbonate and 5.0 g of sodium iodide in 100 ml of acetone. After this time the mixture is filtered and the filtrate is evaporated down. The residue is stirred with ether, suction filtered and dried at 40° C.

Workup

  1. additionadding, after 12 hours
  2. filtrationAfter this time the mixture is filtered
  3. customthe filtrate is evaporated down
  4. stirringThe residue is stirred with ether, suction
  5. filtrationfiltered
  6. customdried at 40° C.

Sources & evidence

ORD record
ord-3646e7470ab44a5bad9b639145f0a7ae
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Reaction notes

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