Methane → HCID 131711198, compound

Participants

Reaction Steps

To a solution of 78.0 g of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt in 500 ml of water is added 17.0 ml of concentrated hydrochloric acid. The solution is cooled to room temperature and 29 g of thiophosgene is added with vigorous stirring. Stirring is continued for 2.5 hours at room temperature. The mixture is treated with activated charcoal, filtered through diatomaceous earth and evacuated by water pump to remove excess thiophosgene. The filtrate is neutralized with 5N sodium hydroxide and evaporated in vacuo to 250 ml. The solution is allowed to crystallize at room temperature, then in an ice bath. The mixture is filtered and the precipitate is washed with ice water, acetone and ether to give a yellow powder. The power is recrystallized from 110 ml of water by warming, then cooling and seeding. The product is collected after standing and the resulting filtrate is concentrated and recrystallized as above. The products are combined and dried by conventional means to yield 36.9 g of 8-isothiocyanato-1,3,6-naphthalenetrisulfonic acid trisodium salt.

Provenance & Evidence