Dibenzoylmethane → HCID 14155098, compound

HRID 1251986Notes

Reaction equation

HRID 1251986 reaction equation
[C:1]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[N:23]=[C:22]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:21][N:20]=1>C(O)(=O)C>[CH2:25]([S:24][C:22]1[N:23]=[C:19]2[N:18]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:20]2[N:21]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 8433DibenzoylmethaneHCID 178509291HCID 178509291, compound

Product 1

HCID 14155098HCID 14155098, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8.40 g (37.5 mmol) of dibenzoylmethane and 7.73 g (37.5 mmol) of 3-amino-5-benzylthio-1,2,4-triazole in 50 ml of glacial acetic acid was heated at reflux for 24 hours. Upon cooling to room temperature the solid which separated was collected by filtration and dried. The product was chromatographed on silica gel (HPLC) eluting with EtOAc-hexane (3:7, v/v) to afford 5.08 g (34%) of the desired product as a colorless solid, m.p. 122.5°-123.5° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 24 hours
  2. customseparated
  3. filtrationwas collected by filtration
  4. customdried
  5. customThe product was chromatographed on silica gel (HPLC)
  6. washeluting with EtOAc-hexane (3:7

Sources & evidence

ORD record
ord-b629151ce566465a916f3a3cf1ca1180
Source dataset
uspto-grants-1988_05
Patent number
US04741764

Reaction notes

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