Triethylamine → N,N-Bis-(4-methoxybenzyl)-(6-chloro-5-trifluoromethylpyridine-2-yl)amine

HRID 545083

反応式

HRID 545083 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[Cl:20][C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C(N(CC)CC)C>CN1CCCC1=O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([F:29])([F:30])[F:28])=[C:21]([Cl:20])[N:22]=2)[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridine

生成物 1

HCID 86605106N,N-Bis-(4-methoxybenzyl)-(6-chloro-5-trifluoromethylpyridine-2-yl)amine

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
120 °C

実験手順

Add bis(4-methoxybenzyl)amine (35.7 g, 138.9 mmol) in 20 mL of N-methylpyrrolidone to a solution of 2,6-dichloro-3-trifluoromethylpyridine (20 g, 92.6 mmol) and triethylamine (19.4 mL, 138.9 mmol) in 100 mL of N-methylpyrrolidone. Raise the temperature to 120° C., and stir the reaction for 14 hours. Quench the reaction mixture by the addition of water (80 mL), followed by extraction with EtOAc (3×70 mL). Wash the combined organic extracts with water (2×70 mL) and brine (70 mL), and dry over anhydrous Na2SO4. Filter the dried extract and concentrate under vacuum to afford the crude product, which is purified by column chromatography to give a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, 1H, J=8.4 Hz), 7.15 (m, 4H), 6.85 (m, 4H), 6.31 (d, 1H, J=8.8 Hz), 4.70 (s, 4H), 3.80 (s, 6H). Mass spec. (436.99, M+H).

後処理

  1. customthe reaction for 14 hours
  2. customQuench the reaction mixture
  3. additionby the addition of water (80 mL)
  4. extractionfollowed by extraction with EtOAc (3×70 mL)
  5. washWash the combined organic extracts with water (2×70 mL) and brine (70 mL)
  6. dry with materialdry over anhydrous Na2SO4
  7. filtrationFilter the dried
  8. extractionextract
  9. concentrationconcentrate under vacuum

出典と根拠

ORDレコード
ord-3472bab536a54267a5eed4ab91871cf4
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

関連ノート

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