Nitric Acid → methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate

HRID 1033159노트

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HRID 1033159 반응식
[Cl:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:10]([F:27])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[N+:28]([O-])([OH:30])=[O:29]>S(=O)(=O)(O)O>[Cl:1][CH:2]([CH2:7][C:8]1[CH:9]=[C:10]([F:27])[C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[CH:12][C:13]=1[N+:28]([O-:30])=[O:29])[C:3]([O:5][CH3:6])=[O:4]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 19025379methyl 2-chloro-3-[3-fluoro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate2회

생성물 1

HCID 19025375methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate수율 28.2%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
10 °C

실험 절차

A mixture of 10.4 grams (0.025 mole) of methyl 2-chloro-3-[3-fluoro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate in 100 mL of concentrated sulfuric acid was stirred for two hours until the methyl propanoate was completely dissolved. The mixture was then cooled to 10° C., and 2.7 grams (0.030 mole) of 70% nitric acid was added dropwise while the temperature of the reaction mixture was held at 10° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature, where it was stirred for one hour. The reaction mixture was then poured into ice-water and stirred until the ice melted. The mixture was extracted with diethyl ether. The extract was washed with water and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 3.2 grams of methyl 2-chloro-3-[5-fluoro-2-nitro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoate, mp 60°-65° C. The NMR spectrum was consistent with the proposed structure.

후처리

  1. dissolutionwas completely dissolved
  2. customwas held at 10° C
  3. additionUpon completion of addition
  4. temperatureto warm to ambient temperature
  5. extractionThe mixture was extracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried with magnesium sulfate
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure to a residue
  10. washElution
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-df3af671788a4370b6cb4731b8c3701a
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310723

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