Dichloromethane → HCID 14324551, compound

HRID 1460811Notes

Reaction equation

HRID 1460811 reaction equation
ClCCl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].[CH2:18]([NH2:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].ClC(Cl)C>C(N(CC)CC)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:34][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:13])=[O:12])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 63651,1-DichloroethaneHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8926Hexadecylamine

Product 1

HCID 14324551HCID 14324551, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To one liter of dichloromethane was added 800 g of 4-chloro-3-nitrobenzenesulfonyl chloride prepared in the above step and the mixture was cooled to 0° C. Then, a mixture of 600 g of hexadecylamine, 251 ml of triethylamine, and 780 ml of dichloroethane was added dropwise to the mixture at 20° C. to 30° C. After performing the reaction for 2 hours at room temperature, the dichloromethane was distilled off from the reaction mixture under reduced pressure and the residue was dissolved in 3 liters of methanol under heating. After gradually cooling the solution to room temperature to form crystals, 3 liters of methanol was added to the solution and the mixture was ice-cooled to deposit crystals which were then recovered by filtration and dried to provide 1020 g of the above-described compound with a yield of 88%. The melting point thereof was 91° C. to 93° C.

Workup

  1. customprepared in the above step
  2. additionwas added dropwise to the mixture at 20° C. to 30° C
  3. customthe reaction for 2 hours at room temperature
  4. distillationthe dichloromethane was distilled off from the reaction mixture under reduced pressure
  5. dissolutionthe residue was dissolved in 3 liters of methanol
  6. temperatureunder heating
  7. temperatureAfter gradually cooling the solution to room temperature
  8. customto form crystals, 3 liters of methanol
  9. additionwas added to the solution
  10. temperaturecooled
  11. filtrationwere then recovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-19e58542923d4ba5b749cded83744063
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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