5-Aminosalicylic Acid → 2-Hydroxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethyl-benzylamino)benzoic acid

HRID 458258

Reaktionsgleichung

Reaktionsgleichung von HRID 458258
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:19][C:20]1[C:27]([F:28])=[C:26]([C:29]([F:32])([F:31])[F:30])[C:25]([F:33])=[C:24]([F:34])[C:21]=1[CH2:22]Br>CN(C=O)C>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:22][C:21]2[C:24]([F:34])=[C:25]([F:33])[C:26]([C:29]([F:30])([F:32])[F:31])=[C:27]([F:28])[C:20]=2[F:19])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 40755-Aminosalicylic AcidHCID 8471TriethylamineHCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide

Produkt 1

HCID 99519552-Hydroxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethyl-benzylamino)benzoic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-aminosalicylic acid (1.02 g, 6.66 mmole, purchased from Aldrich Chemical Company, USA, A7, 980-9) and triethylamine (1 ml) in dried DMF (80 ml) was added 2,3,5,6-tetrafluoro-4-trifloromethylbenzyl bromide (1.23 g, 7.18 mmole) (Aldrich, 40, 640-6) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 2 hr at room temperature and then solvent was removed in vacuo. The reaction mixture was diluted with ethyl acetate and then extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous MgSO4. After evaporation of the solvent, the residue was recrystallized from ether/hexane (1:10) to give 1.60 g (64% yield) of 2-hydroxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid as a white solid.

Aufarbeitung

  1. customsolvent was removed in vacuo
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from ether/hexane (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-d7c8a53bf59f4d8ea62f5a479429024f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189878B2

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