Hydrochloric Acid → Methyl Z-4-[[2-butyl-5-[[1-butyl-3-[(3,5-dimethyl-4-isoxazolyl)methyl]-2,5-dioxo-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate monohydrochloride

HRID 1648518Notes

Reaction equation

HRID 1648518 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[C:7](/[CH:10]=[C:11]2\[NH:12][C:13](=[O:21])[N:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[Cl:39][CH2:40][C:41]1[C:42]([CH3:47])=[N:43][O:44][C:45]=1[CH3:46].Cl>CN(C=O)C.CCOCC>[ClH:39].[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:40][C:41]3[C:42]([CH3:47])=[N:43][O:44][C:45]=3[CH3:46])[C:13](=[O:21])[N:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 11743857Methyl Z-4-[[2-butyl-5-[(1-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl]benzoate

Product 1

HCID 19919836Methyl Z-4-[[2-butyl-5-[[1-butyl-3-[(3,5-dimethyl-4-isoxazolyl)methyl]-2,5-dioxo-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate monohydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[(1-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl]benzoate (1.00 g, 2.281 mmol) in DMF (10 mL) is added K2CO3 (1.580 g, 0.011 moles). After stirring for 15 minutes 4-chloromethyl-3,5-dimethylisoxazole (0.35 g, 2.39 mmol) is added. The mixture is stirred for 24 hours. The solvents were removed under high vacuum. After diluting with ethyl acetate and washing with water and brine the solution is dried over MgSO4. Evaporation in vacuo affords a viscous oil which is dissolved in ether and treated with ethereal HCl to afford a foamy solid upon evaporation in vacuo. This solid is crystallized from ethyl acetate/hexane.

Workup

  1. additionis added
  2. customThe solvents were removed under high vacuum
  3. additionAfter diluting with ethyl acetate
  4. washwashing with water and brine the solution
  5. dry with materialis dried over MgSO4
  6. customEvaporation in vacuo
  7. customaffords a viscous oil which
  8. customto afford a foamy solid
  9. customupon evaporation in vacuo
  10. customThis solid is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e873a82b42e34ffabfb0b039ccf660b2
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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