Hydrazine → [1-(4-Trifluoromethoxyphenyl)-methylidene]-hydrazine

Hydrazine (3.3 mL, 105 mmol) was dissolved in ethanol (10 mL) at room temperature. To this solution was added 4-trifluoromethoxybenzaldehyde (5.0 mL, 35 mmol) dropwise over 25 min. The reaction mixture was stirred an additional 45 min and concentrated under vacuum. The residue was dissolved in ethyl ether (20 mL) and washed with water (10 mL). The water layers were extracted with ethyl ether (3×15 mL), and the combined organic layer was dried over magnesium sulfate, filtered and concentrated to give [4-(trifluoromethoxy)benzylidene]hydrazine (XX) as a yellow oil (6.5 g, 91% yield). 1H NMR (DMSO-d6): δ 7.69 (s, 1H); δ 7.56 (d, J=8.7 Hz, 2H) δ 7.30 (d, J=7.8 Hz, 2H); δ 6.94 (bs, 2H); GC-MS m/z 204 (M+).

1. concentrationconcentrated under vacuum
2. dissolutionThe residue was dissolved in ethyl ether (20 mL)
3. washwashed with water (10 mL)
4. extractionThe water layers were extracted with ethyl ether (3×15 mL)
5. dry with materialthe combined organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-c02e39242dcd45e7a2a591a0202b05ee

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067588B2