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

HRID 458258ノート

反応式

HRID 458258 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d7c8a53bf59f4d8ea62f5a479429024f
出典データセット
uspto-grants-2007_03
特許番号
US07189878B2

反応ノート

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