Ammonia → HCID 21162386, compound

Participants

Reaction Steps

5.5 g of 4-(2-[1-oxo-1,2,3,4-tetrahydroisoquinoline-2-carboxamido]-ethyl)-benzenesulfonamide (melting point 197°-198° C., prepared from 1-oxo-1,2,3,4-tetrahydroisoquinoline-2-(N-2-phenylethyl)-carboxamide [melting point 98°-99° C., prepared from 1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2-phenylethyl isocyanate] and chlorosulfonic acid, with subsequent reaction of the sulfochloride with ammonia) are suspended in 75 ml of acetone and 7.5 ml of 2 N sodium hydroxide solution and the mixture is cooled to 0°-5° C. 2.15 g of cyclohexyl isocyanate in 10 ml of acetone are added dropwise, whilst stirring, and the mixture is then stirred for one hour whilst cooling with ice and for three hours at room temperature. The precipitate is dissolved by adding water. After removing the acetone in vacuo, the aqueous solution which remains is acidified with dilute hydrochloric acid. The N-(4-[2-(1-oxo-1,2,3,4-tetrahydro-isoquinoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-urea which has precipitated is filtered off with suction, reprecipitated once from dilute ammonia solution by means of dilute hydrochloride acid, filtered off with suction, dried and recrystallized from ethanol. The product thus obtained melts at 197°-199° C.

Provenance & Evidence