Methylhydrazine → HCID 15634692, compound

To an ice-cold stirred solution of methylhydrazine (4.6 g, 0.1 mol) in dry pyridine (30 ml) was added methanesulfonyl chloride (44.6 g, 0.39 mol) dropwise, while maintaining the temperature between 0° and 10° C. The reaction mixture was left in a freezer (-10° C.) for 2 days. It was then triturated with a mixture of ice and concentrated hydrochloric acid (1:1, v/v, 100 ml). The precipitate that formed was collected, washed with cold water and dried. This product was stirred with chloroform (200 ml) and filtered. The undissolved material, consisting mainly of 1,2-bis(methylsulfonyl)-1-methylhydrazine, was discarded and the filtrate was treated with decolorizing carbon, filtered and evaporated to dryness in vacuo to give a yellow solid, which was crystallized twice from ethanol (Norit A) to give 5.1 g (18%) of the title compound: m.p. 123°-124° C.; anal. (C4H12N2O6S3) C,H,N; 1H NMR (acetone-d6) δ 3.6 [s, 6H, N2 (SO2CH3)2 ], 3.5 (s, 3H, N--CH3), 3.2 (s, 3H, N1SO2CH3).

1. temperaturewhile maintaining the temperature between 0° and 10° C
2. customIt was then triturated with a mixture of ice and concentrated hydrochloric acid (1:1, v/v, 100 ml)
3. customThe precipitate that formed
4. customwas collected
5. washwashed with cold water
6. customdried
7. filtrationfiltered
8. additionthe filtrate was treated with decolorizing carbon
9. filtrationfiltered
10. customevaporated to dryness in vacuo
11. customto give a yellow solid, which
12. customwas crystallized twice from ethanol (Norit A)

ORD record

ord-f8c6d345ec3d49a4808c58c9e2f24b7f

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05214068