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

HRID 499254

反応式

HRID 499254 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f4a432f52cb142898fb8ff753632850d
出典データセット
uspto-grants-2010_08
特許番号
US07767685B2

関連ノート

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