Thionyl Chloride → HCID 13689056, compound

Participants

Reaction Conditions

Reaction Steps

Other 10-hydroxy-7-methoxy-, 10-methoxy-7-hydroxy-, and 7,10-dimethoxy-5-nitro-2-(substituted)-2H[1]benzothiopyrano[4,3,2-cd]indazoles can be prepared in the manner of Examples 33 through 35 and 54. One such compound is 2-[2-(diethylamino)-ethyl]-7-methoxy-5-nitro-2H[1]benzothiopyrano[4,3,2-cd]indazol-10-ol, hydrochloride salt, mp 267°-270° C. The latter compound is prepared from 1-chloro-5-methoxy-8-hydroxy-4-nitro-9H-thioxanthen-9-one which in turn is prepared as follows: A suspension of 5.8 g (0.016 mol) of 2-[(5-chloro-2-nitrophenyl)thio]-3,6-dimethoxybenzoic acid, 50 ml of toluene, and 3.8 g (0.032 mol) of thionyl chloride was heated under reflux for two hours, concentrated to dryness in vacuo, and dissolved in 50 ml of nitrobenzene. The solution was treated portionwise with 3.6 g (0.026 mol) of AlCl3, keeping the temperature below 35° C. during the addition. The mixture was stirred for two hours at 70° C., chilled in a refrigerator overnight, and poured into 400 ml of ice-cold H2O. The mixture was extracted four times with CH2Cl2 and the extracts were combined, dried (MgSO4), and concentrated in vacuo to dryness. The residue was triturated successively in petroleum ether and hot MeOH, and recrystallized from DMF to give 1.2 g of product, 272°-273° C.

Provenance & Evidence