Iodine → Methanesulfonic acid--1-[(4-methylphenyl)methyl]hydrazine-1-carboxamide (1/1)

Participants

Reaction Conditions

Reaction Steps

A 22-L 4-neck flask was equipped with an overhead stirring apparatus, warming/cooling bath, thermometer probe, condenser, and 500-mL addition funnel. The flask was charged with 2-(Aminocarbonyl)-2-(4-methylphenylmethyl)-hydrazine carboxylic acid, 1,1-dimethylethyl ester (1100 g, 3.94 moles) and dichloromethane (12 L). The mixture was warmed to 30-35° C. to completely dissolve all solids, then cooled to 25-30° C. and methanesulfonic acid (MsOH) (398 g, 4.14 moles) was added over 30 min. The water bath was replaced with a heating mantle and the reaction solution was heated at reflux for 12-20 hours, and, monitored by TLC analysis (Ethyl Acetate 100%; I2, Rf(sm)=0.3, Rf(prod)=0.1) When complete, the reaction mixture was diluted with heptane (4000 mL), cooled to 10-20° C., and stirred for 30 min. After filtration, the cake was washed with heptane (2×1000 mL) and dried in vacuo at 35-45° C., to afford the title compound as a white solid (1070 g, 98.6%). 1H NMR (DMSO-d6, 300 MHz): δ 1.35 (s, 9 H), 2.26 (s, 1 H), 4.45 (br s, 2 H), 6.06 (s, 2 H), 7.10 (s, 4 H), 8.88 (br s, 1 H); Anal. Calcd. for C10H17N3O4 S,: C, 43.62; H, 6.22; N, 15.26; S, 11.64. Found: C, 43.33; H, 6.21; N, 14.97.

Provenance & Evidence