Nitric Acid → 4-Methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine

HRID 457881노트

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HRID 457881 반응식
[N+:1]([O-:4])([OH:3])=[O:2].S(=O)(=O)(O)O.[NH2:10][C:11]1[S:12][C:13]([CH2:17][CH2:18]O)=[C:14]([CH3:16])[N:15]=1.[OH-].[Na+]>CCCCCC.O>[CH3:16][C:14]1[N:15]=[C:11]([NH2:10])[S:12][C:13]=1[CH2:17][CH2:18][O:2][N+:1]([O-:4])=[O:3]

참가 물질

7

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1509432-Amino-4-methyl-5-hydroxyethylthiazole2회

생성물 1

HCID 115574994-Methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

반응 조건

온도
25 °C

실험 절차

Subsequently, 4-methyl-5-(2-nitrooxy-ethyl)-thiazole-2-ylamine was prepared by drop-wise addition of 1.59 grams of nitric acid (70%) to 2.48 grams of cooled sulfuric acid (95–98%) at 0–5° C. over a time period of 20 minutes. Following, 4 grams (0.025 moles) of 2-(2-Amino-4-methyl-thiazol-5-yl)-ethanol were added over a time period of 45 minutes at 0–5° C. After the addition was completed, the reaction mixture was stirred for 3 hours at 25° C., and was then added carefully to 50 ml of cold water. The water solution was turned basic with an aqueous solution of 20% sodium hydroxide and the aqueous phase was extracted with three portions of 75 grams of ethyl acetate. The organic extracts were combined, dried over sodium sulfate, filtered and evaporated to dryness under vacuum. Chromatography of the crude product on silica gel (using a mixture of 8:2 ethyl acetate:hexane as eluent) gave 1.8 grams (35% yield) of the product as orange oil having a purity of 98.5% as determined by gas chromatography.

후처리

  1. additionAfter the addition
  2. extractionthe aqueous phase was extracted with three portions of 75 grams of ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under vacuum
  6. additiona mixture of 8:2 ethyl acetate

출처 및 근거

ORD 기록
ord-ae9837e3ab284df68242e3db92204ad2
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189750B2

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