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

HRID 1094828

反応式

HRID 1094828 の反応式
[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]

参加物

7

反応物 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1509432-Amino-4-methyl-5-hydroxyethylthiazole2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8058Hexane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d4c4abef7430437ca1db300bcb807abc
出典データセット
uspto-grants-2012_03
特許番号
US08134010B2

関連ノート

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