4-Aminobenzyl alcohol → (4-((4-(3-Chlorophenyl)-6-ethyl-1,3,5-triazin-yl)amino)phenyl)methanol

HRID 1508723ノート

反応式

HRID 1508723 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[N:5]=[C:4]([CH2:15][CH3:16])[N:3]=1.[NH2:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=1>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]([CH2:15][CH3:16])[N:3]=[C:2]([NH:17][C:18]3[CH:25]=[CH:24][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 2

HCID 693314-Aminobenzyl alcoholHCID 901116132-Chloro-4-(3-chlorophenyl)-6-ethyl-1,3,5-triazine

生成物 1

HCID 74221497(4-((4-(3-Chlorophenyl)-6-ethyl-1,3,5-triazin-yl)amino)phenyl)methanol収率 16%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
75 °C

実験手順

2-Chloro-4-(3-chlorophenyl)-6-ethyl-1,3,5-triazine (0.140 g, 0.55 mmol) and 4-aminobenzyl alcohol (0.135 g, 1.1 mmol) were suspended in acetic acid (5 mL). The mixture was heated to 75° C. for 1 h. The reaction was cooled, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/ethyl acetate) and then triturated with hexanes to afford the title compound (0.030 g, 16%) as a yellow solid. MW=340.81. 1H NMR (DMSO-d6, 500 MHz) δ 10.24 (s, 1H), 8.42-8.31 (m, 2H), 7.75-7.68 (m, 3H), 7.61 (t, J=7.5 Hz, 1H), 7.36-7.28 (m, 2H), 5.11 (t, J=5.5 Hz, 1H), 4.48 (d, J=5.5 Hz, 2H), 2.78 (q, J=7.5 Hz, 2H), 1.32 (t, J=7.5 Hz, 3H); APCI MS m/z 341 [M+H]+.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/ethyl acetate)
  7. customtriturated with hexanes

出典と根拠

ORDレコード
ord-bacb7a3ff3e340e19b96b16cf4f894d0
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

読み込み中…