Trifluoroacetic acid → HCID 85957959, compound

Participants

Reaction Steps

An excess of trifluoroacetic acid (99%, Acros) was added to 0.2 g of 4-[4-(6-mercapto-hexyloxy)-phenylazo]-benzoic acid t-butyl ester. The mixture was stirred for 5 minutes to dissolve. Excess trifluoroacetic acid was flushed from the vessel using a stream of argon. Acetone was added to the crude mixture to remove unreacted starting materials. The deprotected product acid was solidified by acetone and filtered out. The solid product (compound 2, FIG. 11) was further purified by washing with several portions of acetone. The yield was 90-95%, and product characteristics were: 1H NMR (DMSO-d6) δ 13.08 (broad, 1H), 8.10 (d, J=9 Hz, 2H) 7.89 (dd, J=9 Hz, 4H), 7.11 (d, J=9 Hz, 2H), 4.06 (t, J=6 Hz, 2H), 2.7 (m, 2H), 1.78-1.25 (m, 9H). HR-MS (M+1) gave a mass of 359.1441 compared to the theoretical value of 359.1429 for C19H23O3N2S.

Provenance & Evidence