Dichloromethane → HCID 131722253, compound

HRID 565078Notes

Reaction equation

HRID 565078 reaction equation
[C:1]1(=[O:20])[N:5]([CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7](O)=[O:8])[C:4](=[O:19])[CH:3]=[CH:2]1.C(Cl)[Cl:22]>>[C:1]1(=[O:20])[N:5]([CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([Cl:22])=[O:8])[C:4](=[O:19])[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 18477222HCID 18477222, compound

Product 1

HCID 131722253HCID 131722253, compound

Conditions

Temperature
72.5 °C

Procedure

24.0 g (0.085 mole) maleimidoundecanoic acid were dissolved in 50 ml of dry CH2Cl2 in a 250 ml round bottomed flask fitted with a stirrer, reflux condenser and CaCl2 drying tube, and were treated with 31.0 g (0.24 mole) oxalyl and boiled under reflux for 15 hours at an oil bath temperature of 70 to 75° C. Subsequently, the CH2Cl2 was first distilled off under normal pressure, and the oxalyl chloride was distilled off at 0.01 mbar. On account of its susceptibility to hydrolysis, the dark-coloured residue was not purified further, but was immediately used for further syntheses. Yield: 2.5 g=100% theoretical. The maleimidoundecanoic acid chloride had a purity of 94% as determined by GC/MS.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser and CaCl2 drying tube
  3. additionwere treated with 31.0 g (0.24 mole) oxalyl
  4. distillationSubsequently, the CH2Cl2 was first distilled off under normal pressure
  5. distillationthe oxalyl chloride was distilled off at 0.01 mbar
  6. customOn account of its susceptibility to hydrolysis
  7. customthe dark-coloured residue was not purified further

Sources & evidence

ORD record
ord-92c99bf682f848f6a84166d983bf6ccb
Source dataset
uspto-grants-2001_01
Patent number
US06169186A

Reaction notes

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