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

HRID 2165034Notes

Reaction equation

HRID 2165034 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 liter of dichloromethane was added to 800 g of 4-chloro-3-nitrobenzenesulfonyl chloride and the solution was cooled to 0° C. To the solution was added dropwise a mixture of 600 g of hexadecylamine, 251 ml of triethylamine and 780 ml of dichloromethane at 20° to 30° C. After the reaction mixture was reacted for 2 hours at room temperature, the dichloromethane was distilled off under reduced pressure, and 3 liters of methanol was added to the residue followed by heating to dissolve it. The solution was cooled gradually and after crystals were precipitated at room temperature, 3 liters of methanol was added thereto to further facilitate the crystallization under cooling with ice water, and the crystals were filtered and dried.

Workup

  1. additionTo the solution was added dropwise
  2. customAfter the reaction mixture was reacted for 2 hours at room temperature
  3. distillationthe dichloromethane was distilled off under reduced pressure, and 3 liters of methanol
  4. additionwas added to the residue
  5. temperatureby heating
  6. dissolutionto dissolve it
  7. temperatureThe solution was cooled gradually
  8. customafter crystals were precipitated at room temperature
  9. addition3 liters of methanol was added
  10. customthe crystallization
  11. temperatureunder cooling with ice water
  12. filtrationthe crystals were filtered
  13. customdried

Sources & evidence

ORD record
ord-060b6b1760c249249d8b295adf5d5c8d
Source dataset
uspto-grants-1990_07
Patent number
US04939066

Reaction notes

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