Hydrochloric Acid → HCID 57448161, compound
Reaction equation
[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[C:7]#[N:8])[CH2:3][CH2:2]1.S(C)C.[ClH:16]>C1COCC1>[ClH:16].[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[CH2:7][NH2:8])[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1A (1.50 g, 7.25 mmol) in refluxing THF (72 mL) was added a 2M THF solution of BH3.SMe2 (10.8 mL, 21.7 mmol). After heating at reflux for 2 h, the reaction was cooled to rt and 6M HCl (4.32 mL) was slowly added. The reaction was heated to reflux for 30 min, then cooled to rt, concentrated and azeotroped (3×) with THF/MeOH on a rotary evaporator. The resulting residue was taken up in THF and filtered to provide 1B (1.40 g, 79%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.15 (m, 2H) 1.29 (m, 2H) 2.91 (m, 1H) 4.52 (s, 2H) 7.72 (m, J=7.69, 7.69 Hz, 2H) 7.80 (t, J=6.81 Hz, 1H) 8.04 (d, J=7.91 Hz, 1H).