Hydrochloric Acid → (2E)-3-(2-anilinothiazol-4-yl)acrylaldehyde

HRID 2107267ノート

反応式

HRID 2107267 の反応式
[NH:1]([C:8]1[S:9][CH:10]=[C:11]([CH:13]=[CH:14][CH2:15][OH:16])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.Cl>CS(C)=O>[NH:1]([C:8]1[S:9][CH:10]=[C:11](/[CH:13]=[CH:14]/[CH:15]=[O:16])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 538556963-(2-Anilinothiazol-4-yl)allyl alcohol

生成物 1

HCID 15053531(2E)-3-(2-anilinothiazol-4-yl)acrylaldehyde

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

2.6 g of the crude alcohol thus obtained were dissolved in 20 ml of dimethyl sulfoxide, and 3.4 g of triethylamine were added to the resulting solution. Next, a solution of 5.3 g of a sulfur trioxide pyridine complex in dimethyl sulfoxide (10 ml) was added dropwise to the reaction mixture at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was then poured into water, acidified with 3N hydrochloric acid, and extracted with ethyl acetate. After the extract was dried over anhydrous sodium sulfate, the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography, using as eluent a 10:1 mixture of benzene and ethyl acetate, giving the desired compound as pale yellow crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additiona 10:1 mixture of benzene and ethyl acetate

出典と根拠

ORDレコード
ord-145429a92b7049ba9c4bcbb743566ee3
出典データセット
uspto-grants-1990_06
特許番号
US04933355

反応ノート

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