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Acetic Anhydride → n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide

HRID 404871
ノート
印刷プレビュー

反応式

HRID 404871 の反応式
[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([N:22]4C(=O)C5[C:24](=CC=CC=5)[C:23]4=[O:32])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl.CCCCCC.C(OCC)(=O)C.CO.C(O)C>[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([NH:22][C:23](=[O:32])[CH3:24])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 694391172-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione

生成物 1

HCID 23648576n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide収率 24.2%

試薬・触媒・溶媒 5

HCID 702Ethanol溶媒
HCID 887Methanol溶媒
HCID 6344Dichloromethane溶媒2 回
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of Example 3C (200 mg, 0.41 mmol) at room temperature in dichloromethane (5 mL) was added hydrazine hydrate (197 uL, 4.1 mmol). Ethanol was added until a clear, single phase was formed. After an hour at room temperature, the solvent was removed under vacuum and the reaction mixture was thoroughly dried. To the resulting mixture was added dichloromethane (5 mL), triethylamine (300 uL, 2.15 mmol) and acetic anhydride (150 uL, 1.59 mmol). After two hours at room temperature, methanol was added and the solution was stirred for additional hour. The mixture was concentrated and the product was isolated via silica column chromatography (using a gradient of 25 to 75% ethyl acetate in hexane) and yielded 40 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.23 (m, 3H) 6.83-6.95 (m, 4H) 5.66 (d, J=8.09 Hz, 1H) 5.25-5.43 (m, 1H) 4.52 (heptet, J=6.25 Hz, 1H) 2.00 (s, 3H) 1.57 (d, J=6.99 3 H) 1.35 (d, J=6.25 Hz, 6H), MS (DCI): m/z 403 (M+H).

後処理

  1. customwas formed
  2. waitAfter an hour at room temperature
  3. customthe solvent was removed under vacuum
  4. customthe reaction mixture was thoroughly dried
  5. concentrationThe mixture was concentrated
  6. customthe product was isolated via silica column chromatography (

出典と根拠

ORDレコード
ord-e4623637a0c54002b39fb3769ff31b34
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748627B2

反応ノート

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