Acetic Anhydride → HCID 13712581, compound

HRID 1757943Notes

Reaction equation

HRID 1757943 reaction equation
C([O:8][C:9]([N:11]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]([CH2:23][CH3:24])[C:14](=[O:25])[CH2:13][O:12]1)=O)C1C=CC=CC=1.[C:26](OC(=O)C)(=O)C>[Pd]>[C:9]([N:11]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]([CH2:23][CH3:24])[C:14](=[O:25])[CH2:13][O:12]1)(=[O:8])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20510399HCID 20510399, compound

Product 1

HCID 13712581HCID 13712581, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

0.69 g. (2 mmoles) of 2-benzyloxycarbonyl-3-phenyl-4-ethyl-tetrahydro-1,2,4-oxadiazin-5-one are dissolved in 7 ml. of acetic anhydride, 0.1 g. of a 5%, palladium-on-activated carbon catalyst are added and hydrogen gas is bubbled through the mixture at room temperature under vigorous stirring. The progress of hydrogenation is monitored by thin layer chromatography. As soon as the reaction is complete, the catalyst is filtered off, the filtrate is evaporated to dryness under reduced pressure and the residue is recrystallized from 1 ml. of ethanol. 0.41 g. (82%) of 2-acetyl-3-phenyl-4-ethyl-tetrahydro-1,2,4-oxadiazin-5-one are obtained, melting at 130° C. to 132° C. RfA =0.6.

Workup

  1. customhydrogen gas is bubbled through the mixture at room temperature under vigorous stirring
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. customthe residue is recrystallized from 1 ml

Sources & evidence

ORD record
ord-f2f0afe947c54fb5abe987c32197b40b
Source dataset
uspto-grants-1983_02
Patent number
US04371534

Reaction notes

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