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

HRID 1197686Notes

Reaction equation

HRID 1197686 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[C:17]1([N:23]=[C:24]=[S:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:14])([CH3:15])[C@@H:3]([OH:16])[C@H:2]([NH:1][C:24]([NH:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[S:25])[C:7]=2[CH:8]=1)#[N:13]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 44351603(trans)-1-(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-phenylthioureaYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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) δ 8.5 (s, 1 H), 7.4 (m, 7 H), 6.83 (d, J=8.0 Hz, 1 H), 6.1 (s, 1 H), 6.0 (s, 1 H), 4.0 (s, 1 H), 3.67 (d, J=10.0 Hz, 1 H), 1.5 (s, 3 H), 1.3 (s, 3 H); 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.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction was then concentrated in vacuo
  4. customthe residue was triturated with isopropylether

Sources & evidence

ORD record
ord-67960664a84b42a9842a7c8ae3712505
Source dataset
uspto-grants-1994_01
Patent number
US05276168

Reaction notes

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