4-Hydroxybenzoic acid hydrazide → HCID 136179690, compound

HRID 387470Notes

Reaction equation

HRID 387470 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]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N:23]=[C:24]=S>CO.O=[Hg]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[NH:23][C:24]1[O:7][C:6]([C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:8][N:9]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 1410052-Chloro-5-trifluoromethylphenyl isothiocyanate

Product 1

HCID 136179690HCID 136179690, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 887MethanolSolvent

Procedure

Mercury (II) oxide yellow (1.82 g, 8.41 mmol) was suspended in ca. 50 mL of anhydrous methanol. 4-Hydroxybenzoic acid hydrazide (1.28 g, 8.41 mmol) was added to this bright-orange suspension, followed by 2-chloro-5-trifluoromethyl-phenylisothiocyanate (2.0 g, 8.41 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 solid was re-crystallized from ca. 20 mL of EtOAc. The formed white precipitate was filtered, washed with anhydrous Et2O and dried in vacuo to give the title product as a white solid (2.638 g). Yield 88.1%

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 solid was re-crystallized from ca. 20 mL of EtOAc
  7. filtrationThe formed white precipitate was filtered
  8. washwashed with anhydrous Et2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-10aa19312bd344ceafc78b2ad61ad973
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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