HCID 22748579, compound → HCID 22748581, compound

HRID 267218Notes

Reaction equation

HRID 267218 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(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

4

Reactant 1

HCID 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 on charcoal (1 g.) is hydrogenated at atmospheric pressure and at approximately 20°C. After the absorption of hydrogen (1.9 litres) (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 litres) (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-65508be3eb474df8a0062b29e7bdb2a6
Source dataset
uspto-grants-1976_03
Patent number
US03941798

Reaction notes

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