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

HRID 129178노트

반응식

HRID 129178 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-696b21c5ad774292a137917d4c10da81
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466817

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