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

HRID 2107267노트

반응식

HRID 2107267 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-145429a92b7049ba9c4bcbb743566ee3
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04933355

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