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

HRID 458258노트

반응식

HRID 458258 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d7c8a53bf59f4d8ea62f5a479429024f
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189878B2

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