Hydrochloric Acid → 4-(Bis(2-chloroethyl)amino)benzeneacetic acid

HRID 1855212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855212
[Cl:1][CH2:2][CH2:3][N:4]([CH2:16][CH2:17][Cl:18])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1.[Li+].[OH-].O.Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][N:4]([CH2:16][CH2:17][Cl:18])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 22096817methyl 4-[N,N-bis(2-chloroethyl)amino]phenylacetate

Produkt 1

HCID 253064-(Bis(2-chloroethyl)amino)benzeneacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a round bottom flask was added methyl 2-(4-(bis(2-chloroethyl)amino)phenyl)acetate (B-4) (3.4 g, 11.68 mmol), LiOH (1.7 g, 70.83 mmol), H2O (100 mL) and THF (50 mL). The reaction mixture was stirred at 50° C. for 2 h. After cooled down to r.t., the reaction mixture was adjusted with HCl (1 N) to pH7 and extracted with EtOAc (100 ml*2), the mixture was dried over Na2SO4 and concentrated under reduced pressure. The crude product (2.8 g) was used next step without further purification. LC-MS: (M+H)+=277;

Aufarbeitung

  1. temperatureAfter cooled down to r.t.
  2. extractionextracted with EtOAc (100 ml*2)
  3. dry with materialthe mixture was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customwithout further purification

Quellen und Nachweise

ORD-Eintrag
ord-3c3edc5842ec47cb98f960b6eb15b8bc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962855B2

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