4-Hydroxybenzoic acid hydrazide → 4-[5-(3-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-phenol

HRID 387473

Reaction equation

HRID 387473 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([N:19]=[C:20]=S)[CH:16]=[CH:17][CH:18]=1>CO.O=[Hg]>[Cl:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]2[O:7][C:6]([C:5]3[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 754493-Chlorophenyl isothiocyanate

Product 1

HCID 1361796964-[5-(3-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-phenolYield 89.7%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 887MethanolSolvent

Procedure

Mercury (II) oxide yellow (6.38 g, 29.47 mmol) was suspended in ca. 100 mL of anhydrous methanol. 4-Hydroxybenzoic acid hydrazide (4.48 g, 29.47 mmol) was added to this bright-orange suspension, followed by 3-chlorophenylisothiocyanate (5.0 g, 29.47 mmol). The reaction mixture was brought to reflux and refluxed for 2 hours. The reaction mixture turned pitch-black in color and formed black precipitate. Then it was cooled down to ambient temperature and filtered through a short pad of Celite. Then it was purified by silica gel chromatography using 0% to 20% methanol gradient in EtOAc. Solvent was removed in vacuo and the resulting grey precipitate was re-crystallized from ca. 50 mL of EtOAc. The formed white crystalline solid was filtered, washed with a small amount of EtOAc, anhydrous Et2O and dried in vacuo to give the title product as a white powder (7.606 g). Yield 89.7%.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for 2 hours
  3. customformed black precipitate
  4. filtrationfiltered through a short pad of Celite
  5. customThen it was purified by silica gel chromatography
  6. customSolvent was removed in vacuo
  7. customthe resulting grey precipitate was re-crystallized from ca. 50 mL of EtOAc
  8. filtrationThe formed white crystalline solid was filtered
  9. washwashed with a small amount of EtOAc, anhydrous Et2O
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b6e4b48d93c546c19fd9d73a427b8ecf
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Linked notes

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