Hydrochloric Acid → HCID 9903818, compound

Participants

Reaction Conditions

Reaction Steps

To a mechanically stirred solution of 200.0 g thymine (1.586 mol) in a mixture of 1.33 l water and 65 g sodium hydroxide (1.6 mol) under nitrogen atmosphere were added simultaneously a solution of 378.1 g p-toluenesulphonyl chloride (1.98 mol) in 1.0 l acetonitrile over 60 min and a solution of 95.16 g NaOH (2.38 mol) in 0.330 l water added over 65 min while cooling the reaction in a water bath from an initial temperature of 40° C. to about 35° C. The reaction was stirred an additional 50 min following completion of the additions, and then cooled to 0-5° C. The reaction mixture was then acidified by adding 242 g conc. HCl (2.45 mol) over 10 min. The reaction mixture was stirred an additional 20 min at 0-5° C. followed by vacuum filtration. The solid was vacuum dried at 55° C. overnight. 433.1 g 1-tosylthymine (97% yield, white crystals) was obtained.

Provenance & Evidence