Benzoylhydrazine → HCID 86693873, compound

HRID 627826Notes

Reaction equation

C(S[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])=[N:5][CH3:6])C.[C:14]([NH:22][NH2:23])(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)CCC>[CH3:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[N:5]([CH3:6])[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:22][N:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 100-mL three-neck flask were put the total amount of N-[(ethylsulfanyl)(2-methylphenyl)methylidene]methylamine obtained in Step 3, 7.0 g (51.4 mmol) of benzoylhydrazine, and 30 mL of 1-butanol (1-BuOH), and the mixture was heated and stirred at 120° C. for 15 hours. After reaction for the predetermined time, the solvent was distilled off to give a yellow liquid. This liquid was purified by silica gel chromatography. Ethyl acetate was used as a developing solvent. The obtained fraction was concentrated to give a white solid. This solid was recrystallized with ethyl acetate, so that 7.0 g of a white solid of Hmpptz-Me (abbreviation), an objective 4H-triazole derivative, was obtained in a yield of 58%. A synthesis scheme of Step 4 is shown in (f-4).

Workup

customInto a 100-mL three-neck flask were put
customAfter reaction for the predetermined time
distillationthe solvent was distilled off
customto give a yellow liquid
customThis liquid was purified by silica gel chromatography
concentrationThe obtained fraction was concentrated
customto give a white solid
customThis solid was recrystallized with ethyl acetate, so that 7.0 g of a white solid of Hmpptz-Me (abbreviation)

Sources & evidence

ORD record: ord-f0446b841509480cbc01dfd976f41641
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309458B2

Reaction notes

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