Hydrochloric Acid → HCID 86675801, Verbindung

HRID 59861

Reaktionsgleichung

Reaktionsgleichung von HRID 59861
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:14]=2)=[CH:9][CH:8]=1)=[O:5])#[N:2].[CH:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]=[C:39]=[S:40])([CH3:31])[CH3:30].[H-].[Na+].Cl>CN(C=O)C>[C:1](/[C:3](=[C:39](\[NH:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH:29]([CH3:31])[CH3:30])/[SH:40])/[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:14]=2)=[CH:9][CH:8]=1)=[O:5])#[N:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1420522-Isopropylphenyl isothiocyanateHCID 712093072-cyano-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide

Produkt 1

HCID 86675801HCID 86675801, VerbindungAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The cyanoacetanilide from Step 1 (0.30 g, 0.775 mmol) and 2-isopropylphenyl isothiocyanate (0.16 g, 0.903 mmol) were dissolved in 5 mL of DMF and stirred under N2 while NaH (60%; 62 mg, 1.55 mmol) was added in one portion. The solution was allowed to stir at ambient temperature for 1 h, then it was poured into 20 mL of 1 N HCl. The gummy solid was collected and crystallized from EtOH/water to give 0.32 g (71%) of the title compound as a light yellow solid, mp 159-162° C. 1H NMR (CDCl3) δ 12.56 (s, 1H), 8.56 (s, 1H), 8.18 (d, J=8.7 Hz, 2H), 7.85-7.77 (m, 2H), 7.68-7.60 (m, 3H), 7.45-7.36 (m, 4H), 7.32-7.27 (m, 1H), 7.20 (d, J=7.7 Hz, 1H), 4.42 (s, 1H), 3.11 (heptet, J=6.9 Hz, 1H), 1.26 (d, J=6.9 Hz, 6H); ESIMS m/z 565 ([M+H]+).

Aufarbeitung

  1. additionwas added in one portion
  2. customThe gummy solid was collected
  3. customcrystallized from EtOH/water

Quellen und Nachweise

ORD-Eintrag
ord-ae56a76964784912b088af7c6f27c602
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440964B2

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