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

HRID 727736Notes

Reaction equation

HRID 727736 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. 79 g of potassium carbonate, 400 ml of polyethylene glycol, and 71 g of dimethylsulfuric acid were added to the solution. The admixture was heated under reflux for 5 hours. 240 ml of acetone was added to the solution. 870 ml of water was then added dropwise to the solution in such a manner that the temperature thereof was kept at 40° C. Upon cooling to room temperature, crystallization occurred. The crystals were filtered off, washed with water and methanol, and dried. (Yield: 169 g (97%); m.p.: 74°-75° C.)

Workup

  1. temperatureThe admixture was heated
  2. temperatureunder reflux for 5 hours
  3. customthereof was kept at 40° C
  4. customcrystallization
  5. filtrationThe crystals were filtered off
  6. washwashed with water and methanol
  7. customdried

Sources & evidence

ORD record
ord-c27ab934fb394c539dadf1b85f252755
Source dataset
uspto-grants-1991_09
Patent number
USH0000963

Reaction notes

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