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

HRID 1460420Notes

Reaction equation

HRID 1460420 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-nitrobenzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In 640 ml of acetone, was dissolved 170 g of N-hexadecyl-3-nitro-4-chlorobenzenesulfonamide. Next, 79 g of potassium carbonate, 6 ml of polyethylene glycol 400, and 71 g of dimethyl sulfate were added to the solution, followed by heating at reflux for 5 hours. To the reaction mixture was added 240 ml of acetone, and 870 ml of water was added thereto dropwise at 40° C, followed by cooling to room temperature. The precipitated crystals were collected by filtration, washed successively with water and methanol, and dried to yield 169 g (97%) of the noted compound.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 5 hours
  3. additionwas added
  4. customdropwise at 40° C
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed successively with water and methanol
  7. customdried

Sources & evidence

ORD record
ord-54d10b43d7d74ec0bf1cdf8ebb258587
Source dataset
uspto-grants-1991_12
Patent number
US05071729

Reaction notes

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