Methyl iodide → 5,6-Dichloro-N-[4-(trifluoromethoxy)phenyl]-1H-benzimidazol-2-amine

HRID 1594502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594502
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[F:11][C:12]([F:24])([F:23])[O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[CH:16][CH:15]=1.CI.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][C:12]([F:11])([F:23])[F:24])=[CH:15][CH:16]=3)=[N:10][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 81531DiisopropylethylamineHCID 27773384-(Trifluoromethoxy)phenyl isothiocyanate

Produkt 1

HCID 694169785,6-Dichloro-N-[4-(trifluoromethoxy)phenyl]-1H-benzimidazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4,5-dichloro-1,2-phenylenediamine (2 mmol, 354 mg) and 4-trifluoromethoxyphenyl isothiocyanate (2 mmol, 325 μL) in CH2Cl2 (3 mL) was heated at 40° C. for 4 h. MeI (2.2 mmol, 137 μL) and DIEA (2.0 mmol, 348 μL) were added, and the reaction was brought to 40° C. for 24 h. The reaction mixture was partitioned between CH2Cl2 and brine. The organic phase was dried with Na2SO4 and concentrated in vacuo. Chromatography on silica eluting with 20-40% EtOAc in hexanes provided the product as a tan solid. 1H NMR (500 MHz, d6-DMSO) δ 11.2 (br s, 1H), 9.91 (s, 1H), 7.84 (m, 2H), 7.52 (br s, 1H), 7.34 (d, J=9 Hz, 2H). LC-MS (ESI, Method A): 2.96 min, m/z 362.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was partitioned between CH2Cl2 and brine
  2. dry with materialThe organic phase was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1cae700e06154e37bc090f9f673d19e0
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07301036B2

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