Hydrochloric Acid → HCID 14601408, compound

Participants

Reaction Steps

Methanolic HCl (2.7 mL of a 5.10M sol., 14 mmoles) was added to a solution of N,N-bis(2-methoxyethyl)amine. The solution was stirred for 15 minutes followed by the addition of 5-formylthieno[3,2-b]thiophene-2-sulfonamide (11) (0.742 g,. 3 mmole). The mixture was stirred at room temperature for 24 hours. Sodium cyanoborohydride (0.19 g., 3 mmoles) was added and the mixture was stirred for 24 hours. The mixture was cooled in ice water bath and sodium borohydride (0.38 g., 10 mmoles) was added in divided portions followed by stirring for 2 hours. The reaction was worked up by adding water (20 mL) and evaporating the methanol in vacuo to leave 1 g of crude product. The mixture was chromatographed on a 40×150 mm silica gel column eluting with 7% methanol in chloroform to give 0.66 g of 5-[N,N-bis(2-methoxyethyl)aminomethyl]thieno[3,2-b]thiophene-2-sulfonamide.

Provenance & Evidence