Hydrazine hydrate (1:1) → (E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazine

HRID 1192816Notes

Reaction equation

O.[NH2:2][NH2:3].[F:4][C:5]([F:27])([F:26])[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[N:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)=[N:14]2)=[CH:9][CH:8]=1>CCO.O>[N:2](=[CH:22]/[C:21]1[CH:24]=[CH:25][C:18]([C:15]2[N:16]=[CH:17][N:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][C:5]([F:27])([F:26])[F:4])=[CH:8][CH:9]=3)[N:14]=2)=[CH:19][CH:20]=1)\[NH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 250 mL round-bottomed flask containing hydrazine hydrate (64% aq solution; 7.27 mL, 15.0 mmol) in EtOH (100 mL) at 80° C. was added 4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzaldehyde (5.00 g, 1.50 mmol) portionwise over 5 min. The solution was stirred at reflux for an additional 3 h before being diluted with H2O (300 mL) and cooled to 0° C. The precipitated product was collected by vacuum filtration as a white solid (4.89 g, 93%) mp 222-226° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1H), 8.22 (d, J=8.2 Hz, 2H), 7.84-7.79 (m, 2H), 7.66 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.2 Hz, 2H), 7.29 (s, 1H), 5.63 (br s, 2H); ESIMS m/z 348 (M+H).

Workup

temperatureat reflux for an additional 3 h
filtrationThe precipitated product was collected by vacuum filtration as a white solid (4.89 g, 93%) mp 222-226° C.

Sources & evidence

ORD record: ord-0b79f1654d254c088de7f1870aa3732c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680269B2

Reaction notes

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