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Ammonium Chloride → 2[2-(2-Methylphenoxymethyl)-benzoyl]-imidazole

HRID 567114
ノート
印刷プレビュー

反応式

HRID 567114 の反応式
C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.C([Li])CCC.[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25](N1CCCC1)=[O:26].[Cl-].[NH4+]>O1CCCC1.CO>[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25]([C:6]1[NH:5][CH:9]=[CH:8][N:7]=1)=[O:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 21264588HCID 21264588、化合物HCID 178418339Butyllithium

生成物 1

HCID 153461052[2-(2-Methylphenoxymethyl)-benzoyl]-imidazole収率 63.9%

試薬・触媒・溶媒 2

HCID 887Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-60 °C

実験手順

At −40° C., 6.9 g (0.0405 mol) of N-diethoxymethylimidazole (J. Org. Chem. Vol. 45, No. 20, 1980, page 4040) in 40 ml of tetrahydrofuran are mixed with 11.3 g (0.0405 mol) of 23% pure n-butyllithium, and the mixture is stirred at −60° C. for one hour. At −40° C., 6 g (0.0203 mol) of N-[2-(2-methylphenoxymethyl)-benzoyl]-pyrrolidine are added, and the mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture warms to 20° C. 5 g of ammonium chloride and 50 ml of methanol are added, and the mixture is heated at reflux for 15 minutes. The volatile components are distilled off under reduced pressure and the residue is admixed with water and extracted with ethyl acetate. The organic phase is dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate. 3.79 g (63.8% of theory) of 2[2-(2-methylphenoxymethyl)-benzoyl]-imidazole are obtained.

後処理

  1. customAt −40° C.
  2. stirringthe mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture
  3. customwarms to 20° C
  4. temperaturethe mixture is heated
  5. temperatureat reflux for 15 minutes
  6. distillationThe volatile components are distilled off under reduced pressure
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is dried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-bfb1cab7d81e4942a10ae14ffd0fdfd0
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06177459B1

反応ノート

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