Dichloromethane → HCID 14324551, compound

HRID 2165811Notes

Reaction equation

HRID 2165811 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[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.[Cl:39]CCl>>[Cl:39][C:6]1[CH:5]=[CH:4][C:3]([S:11]([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:13])=[O:12])=[CH:2][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 8926HexadecylamineHCID 230424882-chloro-3-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 14324551HCID 14324551, compound

Conditions

Temperature
0 °C

Procedure

1 liter of dichloromethane was added to 800 g of 4 chloro-3-nitrobenzenesulfonyl chloride and cooled to 0° C. To the solution was added dropwise a mixture comprising 600 g of hexadecylamine, 251 ml of triethylamine and 780 ml of dichloromethane at 20 to 30° C. After being reacted for 2 hours at room temperature, the dichloromethane was removed by distillation under reduced pressure, and 3 liters of methanol was added to the residue and dissolved under heat. The resulting solution was gradually cooled and crystallized out at room temperature. Further, 3 liters of methanol was added and the resulting solution was again crystallized out under ice-cooling, and the crystal precipitated was taken out by filtration and dried. Yield: 1020 g, 88%.

Workup

  1. customAfter being reacted for 2 hours at room temperature
  2. customthe dichloromethane was removed by distillation under reduced pressure, and 3 liters of methanol
  3. additionwas added to the residue
  4. dissolutiondissolved
  5. temperatureunder heat
  6. temperatureThe resulting solution was gradually cooled
  7. customcrystallized out at room temperature
  8. additionFurther, 3 liters of methanol was added
  9. customthe resulting solution was again crystallized out under ice-
  10. temperaturecooling
  11. customthe crystal precipitated
  12. filtrationwas taken out by filtration
  13. customdried

Sources & evidence

ORD record
ord-ee1e3749116e462ea44fbd8321ffe9d5
Source dataset
uspto-grants-1990_07
Patent number
US04942114

Reaction notes

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