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

HRID 259785Notes

Reaction equation

HRID 259785 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 to 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 (t, 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 to an oil (5.4 g)

Sources & evidence

ORD record
ord-9a313664c4694721954fb994c5b09903
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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