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

HRID 1197686ノート

反応式

HRID 1197686 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-67960664a84b42a9842a7c8ae3712505
出典データセット
uspto-grants-1994_01
特許番号
US05276168

反応ノート

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