Nitric Acid → 2-Ethyl-4-methyl-5-(2-nitrooxy-ethyl)-thiazole

HRID 2105958노트

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HRID 2105958 반응식
[N+:1]([O-:4])([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:10]([C:12]1[S:13][C:14]([CH2:18][CH2:19]O)=[C:15]([CH3:17])[N:16]=1)[CH3:11].[OH-].[Na+]>CCCCCC.O>[CH2:10]([C:12]1[S:13][C:14]([CH2:18][CH2:19][O:2][N+:1]([O-:4])=[O:3])=[C:15]([CH3:17])[N:16]=1)[CH3:11]

참가 물질

7

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 184408242-(2-Ethyl-4-methyl-thiazol-5-yl)-ethanol

생성물 1

HCID 116871642-Ethyl-4-methyl-5-(2-nitrooxy-ethyl)-thiazole수율 58%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8058Hexane용매

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온도
2.5 °C

실험 절차

Fifteen (15) ml of nitric acid of (85-90%) were added dropwise to 15 ml of sulfuric acid (95-98%) over a time period of 20 minutes while keeping the temperature at 0-5° C. After 2 hours, 14.3 grams (83.60 mmole) of 2-ethyl-4-methyl-5-thiazoleethanol, prepared as described above, were added, while the temperature was still maintained at 0-5° C., the reaction mixture was stirred for 2 hours at the same temperature, and was then poured carefully onto 125 ml of cold water. The water solution was made basic with a 20% aqueous solution of sodium hydroxide and the aqueous phase was extracted with three portions of 75 grams of dichloromethane. The extracts were combined and dried over sodium sulfate, filtered and evaporated to dryness. Chromatography of the crude product on silica gel (using a mixture of 75:25 ethyl acetate:hexane as an eluent) yielded 10.5 grams (58% yield) of colorless liquid having a purity of 98%, as determined by gas chromatography.

후처리

  1. customat 0-5° C
  2. additionwere added, while the temperature
  3. extractionthe aqueous phase was extracted with three portions of 75 grams of dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additiona mixture of 75:25 ethyl acetate

출처 및 근거

ORD 기록
ord-8d5267e067644429ab05253b85cd42da
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579477B2

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