Isopropanol → 4-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid

HRID 256771

반응식

HRID 256771 반응식
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH3:9])=[N:5][C:4]=1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]([F:24])[CH:13]=1)[CH3:11])=[O:2].CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O.[Cr](O)(O)(=O)=O.CC(O)C>CC(C)=O.S(=O)(=O)(O)O.O>[F:24][C:14]1[CH:13]=[C:12]([CH:10]([C:4]2[N:5]=[C:6]([NH:8][CH3:9])[S:7][C:3]=2[C:1]([OH:27])=[O:2])[CH3:11])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 24425Chromic AcidHCID 19785543HCID 19785543, 화합물HCID 131709961Jones' reagent2회

생성물 1

HCID 197855604-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid수율 20%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 1118Sulfuric Acid용매

실험 절차

5-Formyl-4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazole (1.00 g, 2.9 mmoles) was dissolved in acetone (20 ml). Jones reagent (chromic acid (VI) dissolved in a mixture of concentrated sulfuric acid and water) (2 ml) was added dropwise thereinto while cooling the system with ice, after which it was stirred for one hour. Then, an additional 2 ml of Jones reagent was added dropwise and the resulting mixture was stirred for one hour. A small quantity of 2-propyl alcohol was added to the reaction mixture, it was extracted with ether, and the ether layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain the desired 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid (205 mg, 0.58 mmole, yield 20%) as a white crystalline product.

후처리

  1. additionwas added dropwise
  2. temperaturewhile cooling the system with ice
  3. stirringthe resulting mixture was stirred for one hour
  4. extractionwas extracted with ether
  5. washthe ether layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-9a21952cd5604db0878d4fd1b474390a
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258396

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