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Acetic Acid → HCID 66643683, 화합물

HRID 1923560
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HRID 1923560 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][CH:7]=1)=[O:5])[CH3:2].C(OC(=O)C)(=O)C.C(O)(=O)C.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[CH:35]=O>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH:35]/[C:25]2[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:27][O:28][C:24]=2[CH3:23])=[N:8][CH:7]=1)=[O:5])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 27761445-Methyl-3-phenylisoxazole-4-carboxaldehydeHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

생성물 1

HCID 66643683HCID 66643683, 화합물수율 19.2%

시약·촉매·용매 1

HCID 962Water
용매

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온도
120 °C

실험 절차

2-Methyl-thiazole-5-carboxylic acid ethyl ester (547 mg, 2.92 mmol) was dissolved in acetic anhydride (0.15 mL, 15.5 mmol) and acetic acid (0.04 mL, 2.54 mmol) then 5-methyl-3-phenyl-4-isoxazolecarbaldehyde (500 mg, 2.92 mmol) was added and the reaction mixture warmed to 120° C. After 6 days, the reaction mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 30% ethyl acetate in heptane) to give the title compound (191 mg, 19%) as an off-white solid after trituration with isopropylether. MS: m/e=341.3 [M+H]+.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthen purified by chromatography (silica, 0 to 30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-44193f3d90e4415c8471e640b89b2615
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178522B2

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