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

HRID 1709790Notes

Reaction equation

HRID 1709790 reaction equation
[CH2:1]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)(=[O:20])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:31](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CC(C)=O>[CH3:31][N:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)(=[O:19])=[O:20]

Participants

6

Reactant 4

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

Product 1

HCID 41628334-chloro-N-hexadecyl-N-methyl-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

170 g of N-hexadecyl-3-nitro-4-chlorobenzenesulfonamide was dissolved in 640 ml of acetone, and 79 g of potassium carbonate, 6 ml of polyethylene glycol (average molecular weight: 400), and 71 g of dimethyl sulfate were added thereto, followed by refluxing the mixture for 5 hours under heating. 240 ml of acetone was added to the reaction solution, and 870 ml of water was further dropwise added thereto with stirring and keeping the temperature of the reaction solution at 40° C. Cooling the mixture to room temperature yielded crystals. The crystals were collected by filtration, washed in succession with water and methanol and then dried.

Workup

  1. temperatureby refluxing the mixture for 5 hours
  2. temperatureunder heating
  3. additionwas further dropwise added
  4. customat 40° C
  5. customyielded crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed in succession with water and methanol
  8. customdried

Sources & evidence

ORD record
ord-af4c58be1ccd4327be12ee7b9c14c328
Source dataset
uspto-grants-1990_08
Patent number
US04950764

Reaction notes

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