Dichloromethane → HCID 23434730, compound

Participants

Reaction Steps

The synthesis of 2-(N-methyl)aminomethyl-1,4,8,11-tetrathiacyclotetradecane 5 (as shown in step B of FIG. 1) is performed by the following method. (In FIG. 1, R1 can be methyl (Me) and R2 can be hydrogen (H).) A solution of the previously synthesized crown 2-hydroxymethyl-1,4,8,11-tetrathiacyclotetradecane (0.8 g, 2.7 mmol) in CH2Cl2 (10 mL) is added dropwise to a solution of SOCl2 (0.64 g, 5.4 mmol) in CH2Cl2 (10 mL). After stirring for six hours, the reaction is treated with methanol (1 mL) to quench the excess SOCl2. The solvent is removed by rotary evaporation to yield 2-chloromethyl-1,4,8,11,14-pentathiacycloheptadecane as a yellow oil. The oil is then dissolved in CH3CN (15 mL) and added dropwise to CH3CN (50 mL) that has been saturated with CH3NH2 at 0° C. and charged with Na2CO3 (0.42 g, 4 mmol). The reaction is stirred for 12 hours and then filtered. The solvent is removed by rotary evaporation to yield a yellow oil. The product is purified by column chromatography on silica gel (eluent: 5% methanol in CHCl3) and is isolated as a light yellow oil (0.54 g, 65%).

Provenance & Evidence