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

HRID 1990834노트

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HRID 1990834 반응식
[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]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 587063533-Amino-5-ethoxy-4-iodo-benzaldehyde2회

생성물 1

HCID 866076313-Acetimido-5-ethoxy-4-iodo-benzaldehyde수율 35%

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온도
50 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-71931424d0eb4a34b0e442b6632551d7
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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