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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 1033109
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HRID 1033109 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
-78 °C

실험 절차

To a suspension of 1-Butyl-2,4-imidazolidinedione (0.600 g, 4.17 mmol) in THF (15ml) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-93ab81830fda4bd8a9df3c51914b72a7
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05308853

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