5-Chlorosalicylic Acid → Imd-0354

HRID 1777402

반응식

HRID 1777402 반응식
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[F:12][C:13]([F:26])([F:25])[C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[NH2:17].P(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[F:12][C:13]([F:25])([F:26])[C:14]1[CH:15]=[C:16]([NH:17][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:11])[CH:18]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:20]=1

참가 물질

6

반응물 4

HCID 94475-Chlorosalicylic AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 24387Phosphorus trichlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 5081913Imd-0354수율 57%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To 30 ml of toluene were added 5-chlorosalicylic acid (862 mg, 5 mmol), 3,5-bis(trifluoromethyl)aniline (1.37 g, 6 mmol), and phosphoroustrichloride (755 mg, 5.5 mmol) in the presence of argon gas, followed by stirring for 6 hours through heat-reflux. Sodium hydrogen carbonate was added to the mixture to adjust pH to 7, followed by concentration under reduced pressure. The mixture was dissolved in 60 ml of ethylacetate, which was washed with water (40 ml×2). The organic layer was concentrated under reduced pressure, followed by column chromatography to give 1.09 g of the target compound (yield: 57%).

후처리

  1. temperaturethrough heat-reflux
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe mixture was dissolved in 60 ml of ethylacetate
  4. washwhich was washed with water (40 ml×2)
  5. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-345a9614066d4029ad26aef33ddc90bf
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266872B2

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