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

HRID 2165812Notes

Reaction equation

HRID 2165812 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-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

170 g of 4-chloro-3-nitro-N-hexadecylbenzenesulfonamide was dissolved in 640 ml of acetone, and 79 g of potassium carbonate, 4006 ml of polyethylene glycol and 71 g of dimethylsulfuric acid were then added thereto and heated under reflux for 5 hours. 240 ml of acetone was added thereto, 870 ml of water was added dropwise at 40° C., and the whole was cooled to room temperature, whereby a crystal precipitated out. The crystal was taken out by filtration, washed with water and methanol, and dried. Yield: 169 g, 97%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customwhereby a crystal precipitated out
  4. filtrationThe crystal was taken out by filtration
  5. washwashed with water and methanol
  6. customdried

Sources & evidence

ORD record
ord-f933580a5c424bd984b8cf9fec7ec48b
Source dataset
uspto-grants-1990_07
Patent number
US04942114

Reaction notes

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