Dichloromethane → HCID 19755541, compound

HRID 1460417Notes

Reaction equation

HRID 1460417 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:14])=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].ClCCl.[CH3:18][NH: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][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(N(CC)CC)C>[CH3:18][N: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][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[S:10]([C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[Cl:14])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 206302-Chloro-5-nitrobenzenesulfonyl chlorideHCID 75539N-Methyloctadecylamine

Product 1

HCID 19755541HCID 19755541, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 44 g of 5-nitro-2-chlorobenzenesulfonyl chloride and 100 ml of dichloromethane, was added dropwise a dichloromethane solution containing 48.4 g of methyloctadecylamine and 36.1 ml of triethylamine. After completion of the reaction, the reaction solvent was removed by distillation under reduced pressure, and 300 ml of methanol was added to the residue. The mixture was once heated to dissolve, and then gradually cooled to precipitate crystals, which were collected by filtration and dried to yield 64 g (74%) of the noted compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solvent was removed by distillation under reduced pressure, and 300 ml of methanol
  3. additionwas added to the residue
  4. temperatureThe mixture was once heated
  5. dissolutionto dissolve
  6. temperaturegradually cooled
  7. customto precipitate crystals, which
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-6d9cb6f42278465795c6ab171fd266ad
Source dataset
uspto-grants-1991_12
Patent number
US05071729

Reaction notes

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