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

HRID 528787ノート

反応式

HRID 528787 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.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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-684ff452f35b4f79b29152e27c19e736
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

反応ノート

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