1,2-BIS(METHYLSULFONYL)-1-(2-CHLOROETHYL)HYDRAZINE synthesis

Yield:127792-84-1 88%

Reaction Conditions:

with lithium chloride in N,N-dimethyl-formamide at 60; for 24 h;

Steps:

Synthesis of Compound VNP4090CE A solution of BMH (237 g) and lithium chloride (131 g, 0.55±0.03 g per g of BMH) in N,N-dimethylformamide (DMF, 1,085 mL, 5.0±0.2 mL per g of BMH) was heated on 60° C. bath for 16-24 hr. The reaction completion was monitored by thin layer chromatography (TLC) and an in-process test with ¹H NMR. After cooling on an ice-bath, water (2,300 mL, 20±1 mL per g of BMH) was added into the reaction mixture, and the mixture was kept stirring. A precipitate was formed and filtered. The cake was triturated in hexanes for 2 hr at room temperature, and then filtered. After drying under vacuum the intermediate 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-hydrazine (VNP4090CE) was obtained as pale solids in a yield of 88%. ¹H NMR spectrum (300 MHz) was clean and identical to the compound described in the prior art procedure: DMSO-d₆, δ 9.94 (s, 1H), 3.80 (t, J=6.4 Hz, 2H), 3.65 (br, 2H), 3.13 (s, 3H), and 3.06 (s, 3H). Melting point (Capillary tube): 133-135° C. TLC: developed with 60% ethyl acetate in petroleum ether and visualized by spraying a solution of methanol/water/sulfuric acid (3:3:1, v/v/v) Rf=0.60-0.70.

References:

US8026395,2011,B1 Location in patent:Page/Page column 5