Sodium hydride → 4-Benzyl-7,7-diphenyl-1,4-oxazepan-3-one

HRID 596164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596164
[CH2:1]([N:8]([CH2:13][CH2:14][C:15]([OH:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:14][C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:28][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 20326654N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine

Produkt 1

HCID 203266404-Benzyl-7,7-diphenyl-1,4-oxazepan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The solution of 19.3 g of N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine in 150 ml of dimethylformamide is added dropwise to the suspension of 1.2 g of sodium hydride in 50 ml of dimethylformamide while stirring and cooling with an ice-bath. The mixture is allowed to warm up to room temperature, stirred for 15 hours and evaporated. The residue is partitioned between 150 ml methylene chloride and 50 ml of N hydrochloric acid, the organic layer separated, washed with water, dried, filtered and evaporated. The residue is triturated with diethyl ether and recrystallized from ethanol, to yield the 4-benzyl-3-oxo-7,7-diphenyl-hexahydro-1,4-oxazepine of the formula ##STR7## melting at 185° to 186°.

Aufarbeitung

  1. temperaturecooling with an ice-bath
  2. stirringstirred for 15 hours
  3. customevaporated
  4. customThe residue is partitioned between 150 ml methylene chloride and 50 ml of N hydrochloric acid
  5. customthe organic layer separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated with diethyl ether
  11. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-220e732c0ebe466ebed9812668e1f5d2
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010166

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