1-Butanol → HCID 68380595, compound

HRID 1748960Notes

Reaction equation

HRID 1748960 reaction equation
C(S[C:4](=[N:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[CH:5]([CH3:7])[CH3:6])C.[C:16]([NH:24][NH2:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)CCC>CO>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:4]([CH:5]([CH3:7])[CH3:6])=[N:25][N:24]=[C:16]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 11955BenzoylhydrazineHCID 68380538HCID 68380538, compound

Product 1

HCID 68380595HCID 68380595, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

In a 300 mL recovery flask were put 13 g (44 mmol) of N-[1-(ethylsulfanyl)isobutylidene]-4-bromoaniline, 3.9 g (29 mmol) of benzoylhydrazine, and 40 mL of 1-butanol, and the mixture was heated and refluxed at 130° C. for 10 hours. After that, 1-butanol was distilled off to give a solid. A methanol suspension of this solid was irradiated with ultrasonic waves, and a white solid was collected by gravity filtration, so that 2.8 g of white powder of 4-(4-bromophenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole was obtained in a yield of 28%. The reaction scheme of Step 4 is shown in (b-4) below.

Workup

  1. customIn a 300 mL recovery flask were put
  2. distillationAfter that, 1-butanol was distilled off
  3. customto give a solid
  4. customwas irradiated with ultrasonic waves
  5. filtrationa white solid was collected by gravity filtration, so that 2.8 g of white powder of 4-(4-bromophenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole
  6. customwas obtained in a yield of 28%
  7. customThe reaction scheme of Step 4

Sources & evidence

ORD record
ord-5a01094a2a69470cb3aab8f5adde4919
Source dataset
uspto-grants-2015_10
Patent number
US09155158B2

Reaction notes

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