Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 14324551, compound

HRID 727735Notes

Reaction equation

HRID 727735 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([NH2:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:31][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8471TriethylamineHCID 8926Hexadecylamine

Product 1

HCID 14324551HCID 14324551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1 l of dichloromethane was added to 800 g of 4-chloro-3-nitrobenzenesulfonyl chloride. The admixture was cooled to a temperature of 0° C. A mixture of 600 g of hexadecylamine, 251 ml of triethylamine, and 780 ml of dichloromethane was added dropwise to the solution in such a manner that the temperature thereof was kept at 20° to 30° C. After being allowed to react at room temperature for 20 hours, dichloromethane was removed from the reaction mixture under reduced pressure. The residue was dissolved in 3 l of methanol under heating. The solution was gradually cooled to room temperature where crystallization took place. 3 of methanol was then added to the solution. The solution was cooled with ice to induce crystallization. The crystals were then

Workup

  1. additionwas added dropwise to the solution in such a manner that the temperature
  2. customthereof was kept at 20° to 30° C
  3. customto react at room temperature for 20 hours
  4. customdichloromethane was removed from the reaction mixture under reduced pressure
  5. dissolutionThe residue was dissolved in 3 l of methanol
  6. temperatureunder heating
  7. temperatureThe solution was gradually cooled to room temperature
  8. customwhere crystallization
  9. addition3 of methanol was then added to the solution
  10. temperatureThe solution was cooled with ice
  11. customcrystallization

Sources & evidence

ORD record
ord-647a5af5cc7c4508bb2bdf15c7623320
Source dataset
uspto-grants-1991_09
Patent number
USH0000963

Reaction notes

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