Methane → HCID 20312935, compound

HRID 2420082Notes

Reaction equation

HRID 2420082 reaction equation
[H][H].C([N:10]1[C:15](=[O:16])[N:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:13][CH2:12][O:11]1)C1C=CC=CC=1.C>[Pd](Cl)Cl.C(O)(=O)C>[Cl:24][C:19]1[CH:18]=[C:17]([N:14]2[CH2:13][CH2:12][O:11][NH:10][C:15]2=[O:16])[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

6

Reactant 3

HCID 297MethaneHCID 20312941HCID 20312941, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20312935HCID 20312935, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Hydrogen was passed through a mixture of 3.37 g of 2-benzyl-4-(3',4'-dichlorophenyl)-3-oxo-5,6-dihydro-1,2,4-oxadiazine, 70 ml of acetic acid, 680 mg of animal charcoal and 0.6 ml of a 20% palladium chloride solution until absorption ceased and the mixture was filtered. The filter was washed with acetic acid and the filtrate was poured into ice water. The mixture was extracted with methylene chloride and the organic extracts were dried and evaporated to dryness. The crystalline product was taken up in isopropyl ether to obtain 2.37 g of 4-(3',4'-dichlorophenyl)-3-oxo-5,6-dihydro-1,2,4-oxadiazine melting at 152° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filter was washed with acetic acid
  3. additionthe filtrate was poured into ice water
  4. extractionThe mixture was extracted with methylene chloride
  5. customthe organic extracts were dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-51798954a4ad45b09adeaaec278829e6
Source dataset
uspto-grants-1978_08
Patent number
US04108993

Reaction notes

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