Methylhydrazine → HCID 86722593, compound

Temperature

0 °C

To a stirred solution of methylhydrazine (7.81 g, 169 mmol) in CH2Cl2 (150 mL) cooled to 0° C. was added over 2 hours 4,4,4-trifluorobutanoyl chloride (2.72 g, 16.94 mmol, 0.3 M solution in CH2Cl2) via a syringe pump. After the addition the reaction was stirred at 0° C. for −1 h and then was allowed to warm to ambient temperature. After an additional hour of stirring at ambient temperature, the reaction mixture was poured into a—saturated aqueous solution of Na2CO3 (400 mL). The organic layer was—separated and the—aqueous solution was extracted with additional CH2Cl2 (1×150 mL). The —CH2Cl2 layers—were—combined, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a yellow liquid: 1H NMR (400 MHz, CDCl3) major rotomer δ 3.77 (s, 2H), 3.20 (s, 3H), 2.93-2.85 (m, 2H), 2.48-2.33 (m, 2H); 13C NMR (101 MHz, CDCl3) major rotomer δ 172.81, 127.22 (q, J=276.0 Hz), 29.55 (q, J=29.4 Hz), 25.70 (q, J=3.0 Hz); 19F NMR (376 MHz, CDCl3) major rotomer δ—66.69.

1. additionAfter the addition the reaction
2. temperatureto warm to ambient temperature
3. stirringAfter an additional hour of stirring at ambient temperature
4. customThe organic layer was—separated
5. extractionthe—aqueous solution was extracted with additional CH2Cl2 (1×150 mL)
6. dry with materialThe —CH2Cl2 layers—were—combined, dried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-c76c56ffe7c1485fb2b9f4c33ff4cc23

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09211281B2