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2-Chloro-4-trifluoromethylaniline → N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenylamino)-acetamide

HRID 898564
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 898564
Br.Br[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[C:9]([Cl:21])[CH:8]=1)=[O:5].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[NH2:33]>CN(C=O)C.O>[Cl:21][C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][NH:33][C:24]2[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[CH:28][C:23]=2[Cl:22])[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18]
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Komponenten

5

Edukt 2

HCID 1620012-Chloro-4-trifluoromethylanilineHCID 688779532-Bromo-n-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide

Produkt 1

HCID 10344989N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenylamino)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A solution of 0.228 g (0.511 mmol) of 2-bromo-N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-acetamide-hydrobromide (intermediate product Z1c) and 0.200 g (1.023 mmol) of 2-chloro-4-trifluoromethyl-phenylamine in 5 mL DMF was stirred for 16 hours at 90° C. and then for 24 hours at 120° C. The reaction mixture was cooled to RT, diluted with water and exhaustively extracted with EtOAc. The combined org. extracts were dried over magnesium sulphate and evaporated down i. vac. The residue was dissolved in DMF and purified by HPLC-MS (Stable Bond C18; 3.5 μm; water:acetonitrile:formic acid 9:1:0.01→1:9:0.01 over 9 min).

Aufarbeitung

  1. extractionexhaustively extracted with EtOAc
  2. dry with materialextracts were dried over magnesium sulphate
  3. customevaporated down i
  4. dissolutionThe residue was dissolved in DMF
  5. custompurified by HPLC-MS (Stable Bond C18; 3.5 μm; water:acetonitrile:formic acid 9:1:0.01→1:9:0.01 over 9 min)

Quellen und Nachweise

ORD-Eintrag
ord-2d728526d922429c9e92297b3efee6e1
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07351719B2

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