Ethanol → 1H-Pyrazole-5-carboxylic acid, 4-iodo-1-methyl-, ethyl ester

HRID 588369

반응식

HRID 588369 반응식
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7]([OH:9])=[O:8].[C:11](Cl)(=O)[C:12](Cl)=O.CCO>C(Cl)Cl.CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7]([O:9][CH2:11][CH3:12])=[O:8]

참가 물질

6

반응물 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 6736874-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 601366981H-Pyrazole-5-carboxylic acid, 4-iodo-1-methyl-, ethyl ester수율 89%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid (301.68 g, 1.2 moles) was slurried in 1.2 L of DCM and DMF (2.3 g, 31 mmol) followed by addition of oxalyl chloride (115 mL, 1.3 moles) over 37 minutes and then stirred at room temperature for 3 h. To the resulting solution was added EtOH (750 mL, 12.9 mol) over 5 min followed by stirring at room temperature for 2 h. The crude product solution was concentrated to dryness in vacuo and then reconstituted in 1.2 L of warm heptane followed by filtration. The filtrate was concentrated by removing 500 mL of heptane, resulting in precipitation of solids. The solids were collected via filtration and dried to afford ethyl 4-iodo-1-methyl-1H-pyrazole-5-carboxylate as a white solid (297.6 g, 89% yield).

후처리

  1. stirringby stirring at room temperature for 2 h
  2. concentrationThe crude product solution was concentrated to dryness in vacuo
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated
  5. customby removing 500 mL of heptane
  6. customresulting in precipitation of solids
  7. filtrationThe solids were collected via filtration
  8. customdried

출처 및 근거

ORD 기록
ord-884fe9457511462fa089a6eb1ba3a546
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227956B2

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