1,2-Dichloroethane → Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate

HRID 62721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62721
BrC1C=C(N[C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])C=C(Br)C=1OCC.C(Cl)CCl.[CH2:29]([O:31][C:32]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[C:43]([F:46])([F:45])[F:44])[CH3:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:29]([O:31][C:32]1[C:33]([C:43]([F:44])([F:45])[F:46])=[CH:34][C:35]([NH:36][C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])=[CH:37][C:38]=1[C:39]([F:40])([F:41])[F:42])[CH3:30]

Komponenten

7

Edukt 3

HCID 111,2-DichloroethaneHCID 67041561HCID 67041561, VerbindungHCID 86666596HCID 86666596, Verbindung

Produkt 1

HCID 86666597Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(Methoxycarbonyl)benzoic acid (4) (246 mg, 1.37 mmol) was dissolved in DCM (15 mL) and treated with EDC (654 mg, 3.41 mmol) and DMAP (33 mg, 273 μmol). The resultant mixture was stirred at RT for 15 min. 4-Ethoxy-3,5-bis(trifluoromethyl)aniline (3) (360 mg, 1.32 mmol) was added and the resultant mixture was stirred at RT for 20 h. The mixture was diluted with EtOAc and washed three times with 1 M HCl and then three times with NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (10% EtAOc in isohexane) to afford methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate (5) (150 mg, 28%): m/z 436 [M+H]+ (ES+).

Aufarbeitung

  1. washwashed three times with 1 M HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by silica gel chromatography (10% EtAOc in isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-42b4bc701d9e4e08bbfe555360d54a48
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447028B2

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