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

HRID 500667
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500667
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 57443967Ethyl 6-(2-anilino-2-oxoethyl)-1-benzothiophene-2-carboxylateAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

[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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f0d0072c114348aa81ef211532132299
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772238B2

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