Hydrochloric Acid → N,O-Dibenzylhydroxylamine

HRID 2309755

Reaktionsgleichung

Reaktionsgleichung von HRID 2309755
[CH2:1]([O:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.[OH-].[Na+]>CO>[CH2:10]([NH:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 14798Sodium HydroxideHCID 561973O-benzylbenzaldoximeHCID 5003444Sodium cyanoborohydride2×

Produkt 1

HCID 11063773N,O-Dibenzylhydroxylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 25.0 g O-benzylbenzaldoxime in 100 ml of methanol is mixed with 3.0 g of sodium cyanoborohydride and a few mg of methyl orange indicator. Methanolic hydrochloric acid is added to keep the color of the reaction mixture pale pink (pH=3). After stirring at room temperature for 3 hours, 5.0 more grams of sodium cyanoborohydride is added and the reaction mixture (pH=3) is stirred at room temperature for 12 hours. The reaction mixture is alkalified with aqueous sodium hydroxide and then extracted with methylene chloride. The combined organic layer is washed with water, brine, dried (MgSO4) and evaporated to give the crude product. Liquid chromatography affords the title compound as a colorless liquid.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined organic layer is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-db904e48f3e2476ba66707bebe377f35
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04696964

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