1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → N-{6-[3-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-7-cyano-1,3-benzothiazol-2-yl}acetamide

HRID 1097472

Reaktionsgleichung

Reaktionsgleichung von HRID 1097472
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:18]=[CH:17][C:9]2[N:10]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[S:12][C:8]=2[C:7]=1[C:19]#[N:20].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][C:26]=1[C:34]([F:37])([F:36])[F:35]>CN(C)C=O.C(OCC)(=O)C>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:18]=[CH:17][C:9]3[N:10]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[S:12][C:8]=3[C:7]=2[C:19]#[N:20])=[O:33])=[CH:27][C:26]=1[C:34]([F:35])([F:36])[F:37]

Komponenten

5

Edukt 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 86644686N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide

Produkt 1

HCID 59454498N-{6-[3-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-7-cyano-1,3-benzothiazol-2-yl}acetamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-[6-(3-Aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide (120 mg, 0.369 mmol) produced in Example 12(ii) was dissolved in N,N-dimethylformamide (2 mL), 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (106 mg, 0.48 mmol) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (10 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (5 ml) and saturated brine (5 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (methanol/ethyl acetate=0/100→5/95), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from acetone/n-hexane to give the title compound (114 mg, 57%) as a white powder.

Aufarbeitung

  1. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (5 ml) and saturated brine (5 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)
  6. concentrationthe obtained solution was concentrated under reduced pressure
  7. customThe residue was recrystallized from acetone/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2cd371e6520b431f85544c45cc169692
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143258B2

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