Reaktion #216360

Reaktionsgleichung

(trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

phenylisothiocyanate

→

title compound

Ausbeute 86.1%

(trans)-1-(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-phenylthiourea

Ausbeute 86.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturat reflux for 4 hours
3. 3
   EinengenThe reaction was then concentrated in vacuo
4. 4
   Sonstigethe residue was triturated with isopropylether

Vorschrift

A suspension of (trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (prepared according to Evans et al., J. Med. Chem; 1983, 26, p. 1582 and J. Med. Chem., 1986, 29, p. 2194) (1.0 g, 4.6 mmol) in ethanol (4 ml) under argon was treated with phenylisothiocyanate (0.62 g, 4.6 mmol) and the reaction was heated at reflux for 4 hours. The reaction was then concentrated in vacuo and the residue was triturated with isopropylether to give the title compound as a colorless solid (1.4 g, 85%), m.p. 183°-185° C.; 1H NMR (CDCl3) δ8.5 (s, 1H), 7.4 (m, 7H), 6.83 (d, J=8.0 Hz, 1H), 6.1 (s, 1H), 6.0 (s, 1H), 4.0 (s, 1H), 3.67 (d, J=10.0 Hz, 1H), 1.5 (s, 3H), 1.3 (s, 3H); 13C NMR (CDCl3) 182.5, 156.8, 133.3, 131.9, 130.4, 128.2, 126.0, 125.8, 122.2, 118.8, 118.6, 104.0, 80.5, 75.8, 50.0, 26.3, 18.6; IR (KBr) 1070, 1265, 1491, 1531, 2226, 2978, 3312, 3362 cm--1.

Quelle