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Ammonium Chloride → Methyl 4-[[2-Butyl-5-[(3-Butyl-2,5-Dioxo-4-Imidazolidinyl) Hydroxymethyl]-1H-Imidazol-1-yl]Methyl]Benzoate

HRID 1648510
ノート
印刷プレビュー

反応式

HRID 1648510 の反応式
[CH2:1]([N:5]1[CH2:9][C:8](=[O:10])[NH:7][C:6]1=[O:11])[CH2:2][CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].[CH2:20]([C:24]1[N:25]([CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[C:26]([CH:29]=[O:30])=[CH:27][N:28]=1)[CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>C1COCC1>[CH2:20]([C:24]1[N:25]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=2)[C:26]([CH:29]([CH:9]2[C:8](=[O:10])[NH:7][C:6](=[O:11])[N:5]2[CH2:1][CH2:2][CH2:3][CH3:4])[OH:30])=[CH:27][N:28]=1)[CH2:21][CH2:22][CH3:23]
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

6

反応物 4

HCID 25517Ammonium ChlorideHCID 1185061-Butylimidazolidine-2,4-dioneHCID 2724682Lithium diisopropylamideHCID 10334966Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-YL)methyl]benzoate

生成物 1

HCID 19919823Methyl 4-[[2-Butyl-5-[(3-Butyl-2,5-Dioxo-4-Imidazolidinyl) Hydroxymethyl]-1H-Imidazol-1-yl]Methyl]Benzoate

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-78 °C

実験手順

To a suspension of 1-butyl-2,4-imidazolidinedione (0.600 g, 4.17 mmol) in THF (15 ml) at -78° C. is added lithium diisopropylamide (2.1 equiv.). After stirring for 20 minutes a solution of methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]benzoate (1.250 g, 4.17 mmol) in THF (10 mL) is added dropwise over 10 minutes to form an orange solution. This solution is stirred for a further 20 minutes at -78° C. and is then added to aqueous ammonium chloride. This mixture is evaporated in vacuo and then extracted into ethyl acetate. After washing with water and then brine the solution is dried over Na2SO4. Evaporation in vacuo and chromatography, eluant 5% methanol in chloroform, affords the required product. Recrystallized from ethyl acetate containing traces of methanol.

後処理

  1. additionis added dropwise over 10 minutes
  2. customto form an orange solution
  3. customThis mixture is evaporated in vacuo
  4. extractionextracted into ethyl acetate
  5. washAfter washing with water
  6. dry with materialbrine the solution is dried over Na2SO4
  7. customEvaporation in vacuo and chromatography, eluant 5% methanol in chloroform

出典と根拠

ORDレコード
ord-00259141da294ed9af11f598901f445c
出典データセット
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05436260

反応ノート

読み込み中…

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