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Oxalyl chloride → HCID 70922242, 화합물

HRID 524970
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HRID 524970 반응식
[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:9]([OH:11])=O)[CH2:3][CH2:2]1.[C:12](Cl)(=O)[C:13](Cl)=O>ClCCl.CN(C)C=O>[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:9]([NH:6][C:5]2[CH:4]=[CH:1][CH:2]=[CH:3][C:12]=2[CH3:13])=[O:11])[CH2:2][CH2:3]1
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참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 793254553-cyclopropyl-1H-pyrrole-2-carboxylic acid

생성물 1

HCID 70922242HCID 70922242, 화합물수율 186.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of the 3-cyclopropyl-1H-pyrrole-2-carboxylic acid (50 mg, 0,33 mmol) in dry dichloromethane (0.4 mL) was added a solution of oxalyl chloride (0.04 mL, 0,37 mmol) in 0.3 mL of dichloromethane atroom temperatureand 3 drops of N,N-dimethylformamide. After 1.5 h at this temperature, the mixture was concentrated under vacuum and the residue was redissolved in dichloromethane (1 mL). To this solution was added a solution of o-toluidine in dichloromethane (0,2 mL) and the mixture was stirred at room temperature overnight. The reaction was worked-up diluting with dichloromethane and washing with sodium bicarbonate (2×) and brine. The organic phase was dried and concentrated to give 74 mg of the title compound (88% yield).

후처리

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was redissolved in dichloromethane (1 mL)
  3. additionTo this solution was added a solution of o-toluidine in dichloromethane (0,2 mL)
  4. additionThe reaction was worked-up diluting with dichloromethane
  5. washwashing with sodium bicarbonate (2×) and brine
  6. customThe organic phase was dried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e96c019287c400282873e82871fa601
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340547B2

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