Dimethylformamide → 3-Acetimido-5-ethoxy-4-iodo-benzaldehyde

HRID 1990834ノート

反応式

HRID 1990834 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[I:10])[CH:5]=[O:6].[C:14](Cl)(=[O:16])[CH3:15].C(N(C(C)C)CC)(C)C.CN(C=[O:31])C>>[C:14]1(=[O:16])[N:1]([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=2[I:10])[CH:5]=[O:6])[C:15]1=[O:31]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 587063533-Amino-5-ethoxy-4-iodo-benzaldehyde2 回

生成物 1

HCID 866076313-Acetimido-5-ethoxy-4-iodo-benzaldehyde収率 35%

反応条件

温度
50 °C

実験手順

To a solution of 3-amino-5-ethoxy-4-iodo-benzaldehyde (0.27 g, 0.93 mmol, 1.0 equiv; intermediate 25) and acetyl chloride (0.138 mL, 0.153 g, 1.95 mmol, 2.1 equiv) in anhydrous DMF (5 mL) was added diisopropylethylamine (0.48 mL, 0.36 g, 2.78 mmol, 3.0 equiv) and the mixture stirred at 50° C. for 48 h. Removal of the solvent under reduced pressure and purification of the crude reaction mixture with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (4:1→1:1) yielded 0.11 g (35%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.51 (t, J=7.0 Hz, 3H), 2.29 (s, 3H), 4.19 (q, J=7.0 Hz, 2H), 7.06 (s, 1H), 7.76 (br s, 1H), 8.42 (s, 1H), 9.96 (s, 1H). MS (ISP): 334.0 [M+H]+.

後処理

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification of the crude
  3. customreaction mixture with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (4:1→1:1)

出典と根拠

ORDレコード
ord-71931424d0eb4a34b0e442b6632551d7
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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