Chloroform → BENZOIC ACID, m-(BIS(2-CHLOROETHYL)AMINO)-, METHYL ESTER

HRID 259785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259785
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]

Komponenten

4

Edukt 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 15345697HCID 15345697, Verbindung

Produkt 1

HCID 32688BENZOIC ACID, m-(BIS(2-CHLOROETHYL)AMINO)-, METHYL ESTER

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9a313664c4694721954fb994c5b09903
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523302

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