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

HRID 1883724Notes

Reaction equation

HRID 1883724 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 are added and the mixture is stirred for a total of 4 days at 50° C., while after 12 hours a further 25.9 g of 1-chloro-2dimethylamino-ethane, 49.8 g of potassium carbonate and 5.0 g of sodium iodide in 500 ml of acetone are added and after 36 hours another 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 are added. After this time the mixture is filtered and the filtrate evaporated down. The residue is stirred with ether, suction filtered and dried at 40° C.

Workup

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

Sources & evidence

ORD record
ord-e1bed3ef037b4299b11ac0b4b457c9df
Source dataset
uspto-grants-2004_07
Patent number
US06762180B1

Reaction notes

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