Water → ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate

HRID 528787노트

반응식

HRID 528787 반응식
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.[Cl:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:12][C:3]1[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][NH:6][C:2]=1[CH3:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 77645Ethyl 5-methyl-1H-pyrazole-3-carboxylate

생성물 1

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate수율 95.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of ethyl 5-methyl-1H-pyrazole-3-carboxylate (Maybridge, 4.41 g, 28.6 mmol) in DMF (14 mL) was added N-chlorosuccinimide (3.86 g, 28.9 mmol). The resulting solution was heated at 60° C. for 3 h and then cooled to room temperature. Water was added until a white precipitate formed, and the solid was collected by filtration washing with water. The solid was dissolved in CH2Cl2, washed with water (2×), dried over MgSO4 and concentrated in vacuo to provide the title compound (5.14 g, 90%) as a white solid. 1H NMR (CDCl3) δ 8.03 (s, 1H), 4.42 (q, J=7.0 Hz, 2H), 2.32 (s, 3H), 1.42 (t, J=7.1 Hz, 3H); MS(ESI+) m/z 188.9 (M+H)+.

후처리

  1. temperaturecooled to room temperature
  2. customformed
  3. filtrationthe solid was collected by filtration
  4. washwashing with water
  5. dissolutionThe solid was dissolved in CH2Cl2
  6. washwashed with water (2×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-684ff452f35b4f79b29152e27c19e736
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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