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Aniline → Ethyl 6-(2-anilino-2-oxoethyl)-1-benzothiophene-2-carboxylate

HRID 500667
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HRID 500667 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].CCN=C=NCCCN(C)C.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.NC1C=CC=CC=1>CN(C=O)C>[NH:36]([C:16](=[O:18])[CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=2[CH:14]=1)[C:34]1[CH:35]=[CH:30][CH:31]=[CH:32][CH:33]=1
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참가 물질

6

반응물 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59424238[2-(Ethoxycarbonyl)-1-benzothien-6-yl]acetic acid

생성물 1

HCID 57443967Ethyl 6-(2-anilino-2-oxoethyl)-1-benzothiophene-2-carboxylate수율 66.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

[2-(ethoxycarbonyl)-1-benzothien-6-yl]acetic acid (0.2 g, 0.757 mmol), EDCI (0.22 g, 1.15 mmol) and HOBt (0.16 g, 1.18 mmol) were stirred in DMF (6 mL) for 10 minutes before adding aniline (85 mg, 0.913 mmol). The solution was stirred at room temperature for 3 days. The solvent was removed in vacuo and the residue partitioned between H2O-EtOAc. The aqueous phase was extracted with further portions of EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Et2O was added and the resulting beige solid collected by filtration to give 0.17 g of product (66%). 1H NMR (DMSO-d6) δ 10.21 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.57 (d, J=7.8 Hz, 2H), 7.42 (dd, J=8.4, 1.2 Hz, 1H), 7.27 (t, J=7.2 Hz, 2H), 7.01 (t, J=7.2 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H), 3.78 (s, 2H), 1.31 (t, J=7.2 Hz, 3H).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between H2O-EtOAc
  3. extractionThe aqueous phase was extracted with further portions of EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. additionEt2O was added
  8. filtrationthe resulting beige solid collected by filtration

출처 및 근거

ORD 기록
ord-f0d0072c114348aa81ef211532132299
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772238B2

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