Ethanol → HCID 9863505, compound

To a stirred solution of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine (Shyam, et al.,J. Med. Chem., 1990, 33, 2259-2264) (2.5 g, 0.010 mol) and 2-chloroethyl isocyanate (1.2 g, 0.011 mol) in dry acetonitrile (100 mL) was added triethylamine (1.1 g, 0.011 mol) at room temperature. After an additional 10 min, the reaction mixture was evaporated to dryness in vacuo. The residue was triturated twice with 15 mL quantities of petroleum ether and the petroleum ether layer was discarded each time. The residue was then taken up in ethyl acetate (150 mL) and washed with dilute hydrochloric acid (3×15 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. Upon evaporation of the solvent, a semi-solid residue was obtained which, upon trituration with absolute ethanol, gave a white solid. Recrystallization from ethanol afforded 1.5 g (42.2%) of the title compound: mp 96°-97.5° C.; 1H NMR (acetone-d6) δ 7.0 (br, 1 H, NH), 3.7-4.2 (m, 4 H, SO2NCH2CH2Cl ), 3.5-3.7 (m, 4H, CONHCH2CH2Cl), 3.5 and 3.3 (2s, 6 H, 2 CH3). Anal. (C7H15C12N3O5S2) C, H, N.

1. customthe reaction mixture was evaporated to dryness in vacuo
2. customThe residue was triturated twice with 15 mL quantities of petroleum ether
3. washwashed with dilute hydrochloric acid (3×15 mL)
4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customUpon evaporation of the solvent
7. customa semi-solid residue was obtained which
8. customRecrystallization from ethanol

ORD record

ord-74c6dd7d14f74fb6b11b31b3bb5e9c21

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05637619