Chloroform → Benzoic acid, m-(bis(2-chloroethyl)amino)-, methyl ester

HRID 1598811Notes

Reaction equation

HRID 1598811 reaction equation
O[CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH2:5]CO.O=P(Cl)(Cl)[Cl:20].[CH:23]([Cl:26])(Cl)Cl>>[Cl:20][CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH2:5][CH2:23][Cl:26]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 15345697HCID 15345697, compound

Product 1

HCID 32688Benzoic acid, m-(bis(2-chloroethyl)amino)-, methyl ester

Procedure

A solution of 120a (6.9 g, 29 mmol) in chloroform (50 mL) was added over 2 h to POCl3 (9.9 g) with heating under reflux. After 2.7 h additional reflux, the mixture was cooled in an ice bath, and filtered to remove a white precipitate. The filtrate was neutralized by extraction with saturated aqueous NaHCO3 and chloroform. The organic phase was dried (Na2SO4), filtered, and evaporated no an oil (5.4 g). IR(neat): cm-1 1720. 1H NMR(300 MHz, CDCl3): 7.42-6.87 (m, 4H), 3.90(s, 3H), 3.77 (t, 4H, J=7 Hz), 3.64 4H, J=7 Hz). HR-MS: Calc'd. 276.0558, Found 276.0553.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturethe mixture was cooled in an ice bath
  4. filtrationfiltered
  5. customto remove a white precipitate
  6. extractionThe filtrate was neutralized by extraction with saturated aqueous NaHCO3 and chloroform
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated no an oil (5.4 g)

Sources & evidence

ORD record
ord-80285cea7af64ab68b8e0cace62d4902
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

Loading…