Tetrahydrofuran → HCID 86609906, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[N:6]([CH2:7][CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([OH:18])=[O:17].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O1CC[CH2:32][CH2:31]1>>[C:19]([NH:27][C:28]([NH:1][C:2]1[N:6]([CH2:7][CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:31][CH3:32])=[O:17])=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Komponenten
4
Versuchsvorschrift
A suspension of 5 (2.7 g, 10 mmol) and benzoyl isothiocyanate (1.7 g, 11 mmol) in anhydrous tetrahydrofuran (THF) (20 mL) was refluxed for 12 h. The solvent was evaporated under reduced pressure; the oil residue crystallized adding diethyl ether (30 mL) to afford the pure product 6 (4.07 g, 93%) as a white solid; mp 171-172° C. 1H NMR: δ 1.29 (t, J=7.0, 3H, CH3), 3.97-4.20 (m, 5H, 2CH2+OH, 1H disappears with D2O), 4.58-4.68 (m, 1H, CHO), 7.05-7.98 (m, 10H Ar), 8.02 (s, 1H, H-3), 8.70 (s, 1H, NH, disappears with D2O), 12.05 (s, 1H, NH, disappears with D2O). IR cm−1: 3221 (NH), 3190-2940 (OH), 1708 and 1671 (2 CO). Anal. (C22H22N4O4S) C, H, N, S.