Epichlorohydrin → 3-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile

HRID 1724172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724172
[NH2:1][C@@H:2]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH2:18]([CH:20]1[O:22][CH2:21]1)[Cl:19]>CO>[Cl:19][CH2:18][CH:20]([OH:22])[CH2:21][NH:1][C@@H:2]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Komponenten

4

Edukt 2

HCID 7835EpichlorohydrinHCID 670553723-[(s)-Amino(4-chlorophenyl)methyl]benzonitrile

Produkt 1

HCID 670553403-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 14.0 g (58 mmole) of 3-[(S)-amino(4-chlorophenyl)methyl]benzonitrile and 10.8 g (120 mmole) of epichlorhydrin in 200 mL of methanol was stirred in the dark for 72 hours. The solution was partitioned between CH2Cl2 and water and the layers were separated. The organic layer was dried over Na2SO4 and concentrated to afford the title compound, which was used in the next step without purification; 335 (M+1, 35Cl); 337 (M+1, 37Cl).

Aufarbeitung

  1. customThe solution was partitioned between CH2Cl2 and water
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b53f6c28bbd4da393b7106d0705da3a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485732B2

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