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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
Notes
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Reaction equation

HRID 1648510 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-00259141da294ed9af11f598901f445c
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05436260

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes