1-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazine → Aibmxqrtbasmnp-uhfffaoysa-

HRID 1872404Notes

Reaction equation

HRID 1872404 reaction equation
[CH2:1]([O:7][C:8]1[CH:29]=[CH:28][C:11]([C:12]([NH:14][NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]2[O:13][C:16]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:22]=3)=[N:15][N:14]=2)=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 171784121-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazine

Product 1

HCID 21182386Aibmxqrtbasmnp-uhfffaoysa-Yield 79.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 1-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazine (1.00 g) in phosphorus oxychloride (5 ml) was refluxed for 1 hour. After cooling, the solution was concentrated under reduced pressure. The residue was poured into ice-water and extracted with dichloromethane. The organic layer was washed with water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure. The residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give Methyl 4-[5-(4-n-hexyloxyphenyl)-1,3,4-oxadiazole-2-yl]benzoate (761 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionThe residue was poured into ice-water
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvents were removed under reduced pressure
  9. customThe residue was triturated with acetonitrile
  10. filtrationcollected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-af4d41f039de4336a9d0a77ccb09e54b
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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