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

HRID 499254노트

반응식

HRID 499254 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>CN(C=O)C>[CH2:10]([O:9][C:7]([C:4]1[C:3]([Cl:12])=[C:2]([CH3:1])[NH:6][N:5]=1)=[O:8])[CH3:11]

참가 물질

4

반응물 2

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

생성물 1

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a magnetically stirred solution of ethyl 5-methyl-1H-pyrazole-3-carboxylate (3 mmol) in 10 mL of anhydrous DMF at 0° C. is added N-chlorosuccinimide (4 mmol). The solution is stirred at RT for 5 h. The solvent is concentrated to a half of the original volume, water is added and the reaction mixture is allowed to cool over ice. The solid that precipitates is collected by filtration and purified by crystallization to afford 4-chloro-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid: m.p. 106-107° C.; 1H-NMR (DMSO-d6) δ 1.25-1.32 (t, 3H J=7 Hz), 2.21 (s, 3H), 4.22-4.32 (q, 2H J=7.2), 13.59 (s, 1H).

후처리

  1. concentrationThe solvent is concentrated to a half of the original volume, water
  2. additionis added
  3. temperatureto cool over ice
  4. customThe solid that precipitates
  5. filtrationis collected by filtration
  6. custompurified by crystallization

출처 및 근거

ORD 기록
ord-f4a432f52cb142898fb8ff753632850d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767685B2

반응 노트

불러오는 중…