Hydrochloric Acid → Ethyl 2-(2-bromo-1,3-thiazol-4-yl)acetate

HRID 546879ノート

反応式

HRID 546879 の反応式
N([O-])=O.[Na+].[CH2:5]([O:7][C:8](=[O:16])[CH2:9][C:10]1[N:11]=[C:12](N)[S:13][CH:14]=1)[CH3:6].[Br-:17].[Na+].Cl>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:5]([O:7][C:8](=[O:16])[CH2:9][C:10]1[N:11]=[C:12]([Br:17])[S:13][CH:14]=1)[CH3:6]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 253881Sodium BromideHCID 23668193Sodium Nitrite

生成物 1

HCID 53428667Ethyl 2-(2-bromo-1,3-thiazol-4-yl)acetate収率 6%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 962Water溶媒2 回

実験手順

A solution of sodium nitrite (1.18 g, 0.0171 mol) in water (10 mL) was added dropwise to a mixture of (2-amino-thiazol-4-yl)acetic acid ethyl ester (2.60 g, 0.0140 mol), copper sulfate (6.84 g, 0.0429 mol), sodium bromide (5.89 g, 0.0573 mol) and 9 M hydrochloric acid aqueous solution (30 mL) at 0° C. over 10 minutes. After stirring at the same temperature for 20 minutes, the reaction solution was returned to room temperature over one hour and further stirred at room temperature for two hours. The reaction solution was diluted with water, filtered through celite and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane/ethyl acetate=1/0 to 9/1) to give the title compound (209.3 mg, 6%).

後処理

  1. waitthe reaction solution was returned to room temperature over one hour
  2. stirringfurther stirred at room temperature for two hours
  3. filtrationfiltered through celite
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-444d028b37cb4b77b1e030923c2190b2
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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