Dichloromethane → HCID 14324551, compound

HRID 1460419Notes

Reaction equation

HRID 1460419 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-:3])=[O:2].ClCCl.[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]>C(N(CC)CC)C>[CH2:18]([NH:34][S:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:13])=[O:12])[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]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8926Hexadecylamine

Product 1

HCID 14324551HCID 14324551, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 800 g of 3-nitro-4-chlorobenzenesulfonyl chloride and 1,000 ml of dichloromethane, was added dropwise a dichloromethane solution containing 600 g of hexadecylamine and 251 ml of triethylamine. After completion of the reaction, the reaction solvent was removed by distillation under reduced pressure. The residue was dissolved in 3,000 ml of methanol under heating, followed by gradually cooling to precipitate crystals, which were collected by filtration and dried to give 1,020 g (88%) of the noted compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solvent was removed by distillation under reduced pressure
  3. dissolutionThe residue was dissolved in 3,000 ml of methanol
  4. temperatureunder heating
  5. temperatureby gradually cooling
  6. customto precipitate crystals, which
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-98f48de3076f4c4bb53af5c5be9bae2b
Source dataset
uspto-grants-1991_12
Patent number
US05071729

Reaction notes

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