2-Isopropylphenyl isothiocyanate → 1-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thiourea

HRID 62051ノート

反応式

HRID 62051 の反応式
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]=[C:35]=[S:36])([CH3:27])[CH3:26]>O1CCCC1>[CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([NH:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:23])[F:24])=[CH:9][CH:8]=3)[N:11]=2)=[CH:16][CH:17]=1)=[S:36])([CH3:27])[CH3:26]

参加物

4

反応物 2

HCID 1420522-Isopropylphenyl isothiocyanateHCID 904040894-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylmethanamine

生成物 1

HCID 1186750431-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thiourea収率 68.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of (4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanamine (0.066 g, 0.20 mmol) in tetrahydrofuran (4.0 mL), 1-isopropyl-2-isothiocyanatobenzene (0.048 g, 0.27 mmol) was added. The reaction mixture was stirred in a pre-heated heating block at 80° C. for 4 hours. The reaction mixture was adsorbed onto Celite® and purified via reverse phase chromatography using 5-100% acetonitrile/water as eluent to afford the title compound as a white solid (0.070 g, 68%): 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 1H), 9.30 (s, 1H), 8.07 (dd, J=9.4, 7.3 Hz, 4H), 7.81 (s, 1H), 7.68-7.58 (m, 2H), 7.44 (d, J=8.0 Hz, 2H), 7.36 (d, J=7.7 Hz, 1H), 7.29 (t, J=7.5 Hz, 1H), 7.21 (dd, J=13.2, 6.1 Hz, 2H), 4.78 (s, 2H), 3.11 (s, 1H), 1.15 (d, J=6.9 Hz, 6H); 19F NMR (376 MHz, DMSO-d6) δ −56.96; ESIMS m/z 512 ([M+H]+).

後処理

  1. custompurified via reverse phase chromatography

出典と根拠

ORDレコード
ord-d960f0fbbf234e308c6861b68881e15a
出典データセット
uspto-grants-2016_09
特許番号
US09445594B2

反応ノート

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