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

HRID 1782525

反応式

HRID 1782525 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
2.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f3523d38dea04e2c9576e6728fb67648
出典データセット
uspto-grants-2009_03
特許番号
US07498445B2

関連ノート

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