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Hydrochloric Acid → HCID 67258482、化合物

HRID 907953
ノート
印刷プレビュー

反応式

HRID 907953 の反応式
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][O:9][C:10]2=[O:15])=[O:4].[H-].[Na+].Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH2:8][O:9][C:10]3=[O:15])[C:3](=[O:4])[C:2](=[O:1])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:27][CH:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 67386784HCID 67386784、化合物

生成物 1

HCID 67258482HCID 67258482、化合物収率 66%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-oxo-N-(1-oxo-1,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide (5 g, 11.7 mmol) in DMF (48 mL) was added NaH (0.78 g, 19.5 mmol). The solution was stirring at room temperature for 1.5 hr, followed by the addition of 1-(chloromethyl)-4-methoxy-benzene (2.8 mL). After stirred at 30° C. overnight, the resulting mixture was added water and adjusted to pH=3-4 with 0.5 N aq. HCl. Then ethyl acetate was added, concentrated and filtered, the filtrate was washed by ethyl acetate, the combine ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by flash chromatography on silica gel to obtain the desired compound (4.7 g, yield 66%). LC-MS (ESI) m/z: 402 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.73 (s, 3H), 4.83-5.17 (m, 4H), 6.89-6.91 (d, J=8.8 Hz, 2H), 7.18-7.20 (m, 2H), 7.24-7.26 (m, 1H), 7.38-7.42 (t, 1H), 7.52-7.56 (m, 2H), 7.69-7.71 (m, 1H), 7.75-7.81 (m, 3H).

後処理

  1. stirringAfter stirred at 30° C. overnight
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washthe filtrate was washed by ethyl acetate
  5. washthe combine ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-0bbb3ceb358445558c422f6e6cdf0638
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012976B2

反応ノート

読み込み中…

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