Methane → HCID 22748581, compound

HRID 1390203Notes

Reaction equation

HRID 1390203 reaction equation
[CH:1]([C:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[N+:17]([O-])=[O:18])[N:5]=1)([CH3:3])[CH3:2].C>C(OCC)(=O)C.[Pd]>[CH:1]([C:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[NH:17][OH:18])[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 297MethaneHCID 22748579HCID 22748579, compound

Product 1

HCID 22748581HCID 22748581, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-isopropyl-3-(2-nitro-4-chlorophenyl)-1,3,4-oxadiazolin-2-one (16 g.) in ethyl acetate (130 cc.) containing 3% w/w palladium of charcoal (1 g.) is hydrogenated at atmospheric pressure and at approximately 20° C. After the absorption of hydrogen (1.9 liters) (70% of the theoretical amount), the reaction is stopped and the reaction mixture is filtered. The filtrate is concentrated under reduced pressure and the residue taken up in benzene (50 cc.); the crystals obtained are filtered off and washed with benzene (15 cc.). 5-Isopropyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one (7.2 g.) which melts at 138°-140° C., is obtained. The benzene filtrate is recycled and is subjected to an operation identical to that described above. 5-Isopropyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one (2.9 g.), which melts at 138°-140° C., is obtained.

Workup

  1. customis hydrogenated at atmospheric pressure and at approximately 20° C
  2. customAfter the absorption of hydrogen (1.9 liters) (70% of the theoretical amount), the reaction
  3. filtrationthe reaction mixture is filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe crystals obtained
  6. filtrationare filtered off
  7. washwashed with benzene (15 cc.)

Sources & evidence

ORD record
ord-1406af3951c143c29ba354e909fbabdd
Source dataset
uspto-grants-1979_02
Patent number
US04138404

Reaction notes

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