Sodium hydride → 3-{2-[2-(4-tert-Butyl-phenyl)-thiazol-4-ylmethoxy]-ethyl}-phenyl amine

HRID 585173

反応式

HRID 585173 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.Cl[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[S:18][CH:19]=1>C1OCCOCCOCCOCCOC1.C1COCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:18][CH:19]=[C:15]([CH2:14][O:3][CH2:4][CH2:5][C:6]3[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=3)[N:16]=2)=[CH:25][CH:24]=1)([CH3:29])([CH3:28])[CH3:27]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 149389872-(3-Aminophenyl)ethan-1-olHCID 223401634-Chloromethyl-2-(4-tert-butyl phenyl)thiazole

生成物 1

HCID 223401293-{2-[2-(4-tert-Butyl-phenyl)-thiazol-4-ylmethoxy]-ethyl}-phenyl amine収率 34.1%

試薬・触媒・溶媒 2

HCID 3633615-Crown-5触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 0.027 g (1 mmol) of 95% sodium hydride and 0.5 drop of 15-crown-5 in 20 mL of THF was added dropwise a solution of 0.139 g (1 mmol) of 3-(2-hydroxy ethyl)phenyl amine at 0° C. After stirring for 0.5 hr 0.28 g (1.1 mmol) of 4-chloromethyl-2-(4-tert-butyl phenyl)thiazole was added in one portion. The mixture was stirred at room temperature for 5 hr. At the end of this time, the solution was concentrated and the residue washed with 10 ml of saturated ammonium chloride and extracted 2 times with 30 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to recover an oil, which was purified by column chromatography on SiO2 with 30% ethyl acetate:hexane elution to provide 0.125 g of product as an oil, used in the next step without further purification. NMR (400 MHz, DMSO-d6) δ 7.83 (d, J=8 Hz, 2H, ArH), 7.50 (d, J=8 Hz, 2H, ArH), 7.45 (s, 1H, N═CH) 7.08 (t, J=8 Hz, 1H, H5), 6.63 (d, J=8 Hz, 1H, H4), 6.54 (s, 1H, H2), 6.51 (d, J=8 Hz, 1H, H6) 4.59 (s, 2H, OCH2), 3.71 (t, J=7 Hz, 2H, OCH2), 2.87 (t, J=7 Hz, 2H, ArCH2), 1.30 (s, 9H, t-bu).

後処理

  1. additionwas added in one portion
  2. concentrationAt the end of this time, the solution was concentrated
  3. washthe residue washed with 10 ml of saturated ammonium chloride
  4. extractionextracted 2 times with 30 mL of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto recover an oil, which
  8. customwas purified by column chromatography on SiO2 with 30% ethyl acetate
  9. washhexane elution

出典と根拠

ORDレコード
ord-4ddccf872829470bbdbd5e4166f27fea
出典データセット
uspto-grants-2005_08
特許番号
US06930131B2

関連ノート

読み込み中…