Hydrochloric Acid → 1-[(3-Acetylphenyl)methyl]-3-(4-chlorophenyl)urea

HRID 64230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64230
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3([CH3:25])OCC[O:21]3)[CH:15]=2)=[O:11])=[CH:5][CH:4]=1>C1COCC1>[C:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=1)=[O:11])(=[O:21])[CH3:25]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 715005361-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)urea

Produkt 1

HCID 469169831-[(3-Acetylphenyl)methyl]-3-(4-chlorophenyl)ureaAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 2N HCl solution was added to a solution of 22 (165 mg, 0.479 mmol) in THF (2 mL). The mixture was refluxed for several hours until the starting materials were consumed. The reaction mixture was allowed to cool to room temperature, quenched with solid NaHCO3, and then the volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by chromatography to give 23 (144 mg, 100%) 1H NMR (DMSO-d, 400 MHz) δ 4.44 (d, J=5.6 Hz, 2H), 5.37 (t, J=3.7 Hz, 1H), 6.83 (s, 1H), 7.20-7.26 (5H, m), 7.40 (t, J=7.6 Hz, 1H), 7.50 (d, J=7.2 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.85 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 27.45, 43.13, 119.85, 125.21, 127.11, 127.59, 129.13, 129.37, 132.61, 137.49, 140.07, 141.68, 155.73, 198.58; ESI-HRMS for C16H16N2O2Cl (M+H)+ calcd. 303.0900. found 303.0907.

Aufarbeitung

  1. temperatureThe mixture was refluxed for several hours until the starting materials
  2. customwere consumed
  3. customquenched with solid NaHCO3
  4. customthe volatiles were removed under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aab32b7f591a4ec392ac4e45a7d95478
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447134B2

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