4-Hydroxybenzoic acid hydrazide → HCID 136041855, compound

HRID 387467Notes

Reaction equation

HRID 387467 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:18]=[CH:17][C:16]([N:19]=[C:20]=S)=[CH:15][CH:14]=1>CO.O=[Hg]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([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:15][CH:14]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 136041855HCID 136041855, compound

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 887MethanolSolvent

Procedure

Mercury (II) oxide yellow (6.38 g, 29.47 mmol) was suspended in ca. 70 mL of anhydrous methanol. 4-Hydroxybenzoic acid hydrazide (4.48 g, 29.47 mmol) was added to this bright-orange suspension, followed by 4-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 through a short pad of silica gel. Then methanol was removed in vacuo and the resulting grey precipitate was re-crystallized from ca. 40 mL of EtOAc. The formed white precipitate was filtered, washed with a small amount of EtOAc and dried in vacuo to give the title product as a white powder.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for 2 hours
  3. customformed black precipitate
  4. filtrationfiltered through a short pad of Celite
  5. customThen methanol was removed in vacuo
  6. customthe resulting grey precipitate was re-crystallized from ca. 40 mL of EtOAc
  7. filtrationThe formed white precipitate was filtered
  8. washwashed with a small amount of EtOAc
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1f9cabff9abd421e9e92da29894d6039
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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