HCID 15907743, compound → HCID 15907744, compound

HRID 1458694Notes

Reaction equation

HRID 1458694 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([N:18]([CH2:22][CH2:23][Cl:24])[CH2:19][CH2:20][Cl:21])[CH:17]=1)[C:11]([O:13]C)=[O:12])[CH2:5][CH2:6][Cl:7]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([N:18]([CH2:19][CH2:20][Cl:21])[CH2:22][CH2:23][Cl:24])[CH:17]=1)[C:11]([OH:13])=[O:12])[CH2:5][CH2:6][Cl:7]

Participants

3

Reactant 1

HCID 15907743HCID 15907743, compound

Product 1

HCID 15907744HCID 15907744, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1.59 g (3.82 mmol) of methyl 3,5-bis[N,N-bis(2-chloroethyl)amino]benzoate in 48 ml of concentrated hydrochloric acid was heated at 50° C. for 5 hours. After completion of the reaction, the suspension was extracted with methylene chloride. The extract was washed with an aqueous solution of sodium hydrogencarbonate and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and was then concentrated. The resultant residue was purified by flush chromatography (methanol/chloroform=1/20), whereby 1.01 g of the title compound were obtained as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionthe suspension was extracted with methylene chloride
  3. washThe extract was washed with an aqueous solution of sodium hydrogencarbonate
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. concentrationwas then concentrated
  6. customThe resultant residue was purified
  7. customby flush chromatography (methanol/chloroform=1/20)

Sources & evidence

ORD record
ord-3fd4d091491e4af8ac6389d5f9a17c81
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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