Water → 4-chloro-N-hexadecyl-N-methyl-3-nitrobenzenesulfonamide

HRID 1588381Notes

Reaction equation

HRID 1588381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:28]([O-:30])=[O:29].[C:31](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:9])=[O:10])=[CH:4][C:3]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14324551HCID 14324551, compound

Product 1

HCID 41628334-chloro-N-hexadecyl-N-methyl-3-nitrobenzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In 640 ml of acetone was dissolved 170 g of 4-chloro-3-nitro-N-hexadecylbenzenesulfonamide obtained in the above step and after adding thereto 79 g of potassium carbonate, 6 ml of polyethylene glycol (average molecular weight: 400), and 71 g of dimethylsulfuric acid, the mixture was refluxed for 5 hours. To the reaction mixture was added 240 ml of acetone and after adding dropwise 870 ml of water to the mixture at 40° C., the mixture was cooled to room temperature, whereby crystals deposited. The crystals thus formed were recovered by filtration, washed with water and then methanol, and dried to provide 169 g of the above-described compound with a yield of 97%. The melting point thereof was 74° C. to 75° C.

Workup

  1. customobtained in the above step
  2. additionafter adding
  3. customThe crystals thus formed
  4. filtrationwere recovered by filtration
  5. washwashed with water
  6. dry with materialmethanol, and dried

Sources & evidence

ORD record
ord-f1b5742e673e47b28d657c222aea0dd5
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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