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Trimethylamine → Methyl 3-[[5-bromo-2-(trifluoromethyl)benzoyl]amino]-2,4-dimethyl-benzoate

HRID 239990
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 239990
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.N[C:16]1(C)[CH:25]=[C:24](C)[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH2:17]1.C[N:29]([CH3:31])C.[CH3:32]CCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([NH:29][C:31]1[C:17]([CH3:32])=[C:18]([CH:23]=[CH:24][C:25]=1[CH3:16])[C:19]([O:21][CH3:22])=[O:20])=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1146TrimethylamineHCID 111923Propylphosphonic anhydrideHCID 509981405-Bromo-2-trifluoromethylbenzoic acidHCID 86707353Methyl 3-amino-3,5-dimethylbenzoate

Produkt 1

HCID 86707375Methyl 3-[[5-bromo-2-(trifluoromethyl)benzoyl]amino]-2,4-dimethyl-benzoateAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-2-(trifluoromethyl)benzoic acid (1.0 g, 3.53 mmol) in CH2Cl2 (6 ml) at room temperature are added methyl 3-amino-3,5-dimethylbenzoate (0.44 g, 2.47 mmol, see preparation 12) and trimethylamine (1.0 ml, 7.06 mmol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 5.6 ml, 8.83 mmol) is added via syringe. After 14 hours at ambient temperature, the reaction mixture is diluted with CH2Cl2, washed with water and brine. The organic layers are combined and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 20% ethyl acetate in hexanes to give the title compound as a white solid (0.6 g, 39%).

Aufarbeitung

  1. waitAfter 14 hours at ambient temperature
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-f428251c514c41e1818ff8999a0b1fdb
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642768B2

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