Norchlorambucil → HCID 22096791, compound

HRID 1458703Notes

Reaction equation

HRID 1458703 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7].C(Cl)(=O)C([Cl:22])=O>ClCCCl>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([Cl:22])=[O:18])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7]

Participants

4

Reactant 2

HCID 23198NorchlorambucilHCID 65578Oxalyl chloride

Product 1

HCID 22096791HCID 22096791, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-[4-[N,N-Bis(2-chloroethyl)amino]phenyl]propionic acid (0.24 g; 0.83 mmol) was dissolved in 5 ml of 1,2-dichloroethane, followed by the dropwise addition of 0.22 ml (2.58 mmol; 3.1 equivalents) of oxalyl chloride (with ice-cooling from an intermediary time point due to violent exotherm). After completion of the dropwise addition, the temperature of the resultant mixture was allowed to rise again to room temperature, at which the mixture was stirred for 3 hours and then allowed to stand overnight. The mixture was thereafter concentrated under reduced pressure, whereby the title compound was obtained in a crude form. The crude compound was provided for use in the next reaction without purification.

Workup

  1. temperaturecooling from an intermediary time point due to violent exotherm)
  2. additionAfter completion of the dropwise addition
  3. customto rise again to room temperature, at which
  4. waitto stand overnight
  5. concentrationThe mixture was thereafter concentrated under reduced pressure, whereby the title compound
  6. customwas obtained in a crude form

Sources & evidence

ORD record
ord-0132db4d5f4d461abb07874188aed658
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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