Triethylamine → HCID 66875916, Verbindung

HRID 631713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631713
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[N:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C1CCCCC1>[CH:1]1([C:4]2[CH:8]=[C:7]([NH:9][C:24](=[O:25])[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 27580103-Cyclopropyl-1-phenyl-1H-pyrazol-5-amine

Produkt 1

HCID 66875916HCID 66875916, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-cyclopropyl-1-phenyl-1H-pyrazol-5-amine (1.00 g, 5.03 mmol) and triethylamine (0.66 g, 6.53 mmol) at rt, was added phenyl chloroformate (0.94 g, 6.01 mmol). The reaction mixture was stirred at rt for 15 h. The reaction mixture was partitioned between a mixture of dichloromethane (20 mL) and water (20 mL) and the organic layer was washed thrice with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give yellow oil. Trituration with cyclohexane afforded phenyl 3-cyclopropyl-1-phenyl-1H-pyrazol-5-ylcarbamate (1.01 g, 63%) as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ 10.05 (s, 1H), 6.71-7.55 (m, 10H), 6.18 (s, 1H), 1.92 (m, 1H), 0.91 (m, 2H), 0.73 (m, 2H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between a mixture of dichloromethane (20 mL) and water (20 mL)
  2. washthe organic layer was washed thrice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-5e983ec6a215430ca81246b20817a0c4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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