Triethylamine → N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide

HRID 607388노트

반응식

HRID 607388 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.[C:14]([C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1)#[CH:15].CCN(CC)CC>C1COCC1>[C:14]([C:16]1[CH:17]=[C:18]([NH:22][C:7]([C:3]2[O:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[O:9])[CH:19]=[CH:20][CH:21]=1)#[CH:15]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 781273-Methyl-2-furoic acidHCID 104682Benzenamine, 3-ethynyl-

생성물 1

HCID 51337833N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A dry 25 mL flask was charged with 3-methylfuran-2-carboxylic acid (0.500 g, 3.46 mmol) and thionyl chloride (10 mL). The reaction was heated to 50° C. and allowed to react for 2 h. The reaction was then cooled to room temperature and concentrated affording the crude acid chloride. The acid chloride was then dissolved in THF (5 mL) and 3-ethynyl-phenylamine (0.41 g, 3.47 mmol) was added followed by NEt3 (0.95 mL, 7 mmol). The mixture was allowed to stir at 55° C. for 3 hours and the cooled to room temperature. The reaction was then partitioned between EtOAc and water. The organic layer was then washed once with 1M HCl (5 mL) and then once with saturated aqueous NaHCO3 (5 mL). The organic extracts were then concentrated to give the title compound as a light brown solid (631 mg, 2.80 mmol, 81%).

후처리

  1. customto react for 2 h
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated
  4. customaffording the crude acid chloride
  5. temperaturethe cooled to room temperature
  6. customThe reaction was then partitioned between EtOAc and water
  7. washThe organic layer was then washed once with 1M HCl (5 mL)
  8. concentrationThe organic extracts were then concentrated

출처 및 근거

ORD 기록
ord-6fdd17e6469144dd9a50ca417041ee8c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915443B2

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