Dichloromethane → HCID 14324551, compound

HRID 728523Notes

Reaction equation

HRID 728523 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 88%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

800 g of 3-nitro-4-chlorobenzenesulfonyl chloride and 1,000 ml of dichloromethane were mixed, and thereto was added dropwise a dichloromethane solution containing 600 g of hexadecylamine and 251 ml of triethylamine. After the completion of the reaction, the solvent used was distilled away under reduced pressure, and the residue was dissolved under heating in 3,000 ml of ethanol. Upon gradual cooling, crystals separated out. These crystals were filtered off, and dried. Yield: 1,020 g, Percent yield: 88%, Melting point: 91°-93° C.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent used was distilled away under reduced pressure
  3. dissolutionthe residue was dissolved
  4. temperatureunder heating in 3,000 ml of ethanol
  5. customUpon gradual cooling, crystals separated out
  6. filtrationThese crystals were filtered off
  7. customdried

Sources & evidence

ORD record
ord-4846c56c38aa4f3bade244b775248223
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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