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

HRID 728524Notes

Reaction equation

HRID 728524 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

170 g of N-hexadecyl-3-nitro-4-chlorobenzenesulfonamide was dissolved in 640 ml of acetone, and thereto were added 79 g of potassium carbonate, 6 ml of Polyethylene Glycol 400 and 71 g of dimethyl sulfate. The resulting mixture was heated under reflux for 5 hours. To the resulting reaction mixture, 240 ml of acetone was added, and then 870 ml of water was added dropwise. Upon cooling to room temperature, crystals were deposited. The crystals were filtered off, washed successively with water and methanol, and then dried. Yield: 169 g, Percent yield: 97%, Melting point: 74°-75° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. additionwas added
  4. filtrationThe crystals were filtered off
  5. washwashed successively with water and methanol
  6. customdried

Sources & evidence

ORD record
ord-f8f07d5c8c6f4eaa8fb3b8b1acdc3a0b
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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