Chlorosuccinimide → HCID 53855111, compound

HRID 2292502Notes

Reaction equation

HRID 2292502 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[CH3:2].[Cl:33]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[Cl:33])=[CH:15][CH:16]=1)[CH3:32]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 67648799HCID 67648799, compound

Product 1

HCID 53855111HCID 53855111, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Combine (E and Z)-1-[4-(6-diethylaminohexoxy)phenyl]-1,2-diphenyl-ethylene (2.17 g, 5.07 mmol), N-chlorosuccinimide (0.745 g, 5.57 mmol), and chloroform (40 mL). Heat to reflux for 18 hours. Cool to ambient temperature. Add N-chlorosuccinimide (0.745 g, 5.57 mmol). Heat to reflux. After 2 hours evaporate in vacuo. Chromatograph on silica gel eluting with 10% methanol/dichloromethane. Combine product containing fractions and concentrate in vacuo to give the title compound. Separate the isomers by HPLC, 90 mg per injection, using a Waters and Associates μPorasil column (19 mm by 300 mm), eluting with 80/20/0.2 chloroform/hexane/triethylamine at 20 mL/minute to give (E)-1-[4-(6-diethylaminohexoxy)phenyl]-1,2-diphenyl-2-chloro-ethylene and (Z)-1-[4-(6-diethylaminohexoxy)phenyl]-1,2-diphenyl-2-chloro-ethylene.

Workup

  1. temperatureHeat
  2. temperatureto reflux for 18 hours
  3. temperatureHeat to reflux
  4. customAfter 2 hours evaporate in vacuo
  5. additionCombine product containing fractions
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-17fa73cb70ef4fdca88ae9831c6fe853
Source dataset
uspto-grants-1997_11
Patent number
US05684004

Reaction notes

Loading…