Hydrochloric Acid → HCID 67806015, compound

HRID 1033119Notes

Reaction equation

HRID 1033119 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)[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+].[ClH:50]>CN(C=O)C.CCOCC>[ClH:50].[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11757908HCID 11757908, compound

Product 1

HCID 67806015HCID 67806015, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[[1-butyl-3-(2-naphthalenylmethyl)-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 1-bomomethylnaphthalene (0.53 g, 2.40 mmol) is added. The mixture is stirred for 24 hours then 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/ether.

Workup

  1. additionis added
  2. stirringThe mixture is stirred for 24 hours
  3. customthe solvents were removed under high vacuum
  4. additionAfter diluting with ethyl acetate
  5. washwashing with water and brine the solution
  6. dry with materialis dried over MgSO4
  7. customEvaporation in vacuo
  8. customaffords a viscous oil which
  9. customto afford a foamy solid
  10. customupon evaporation in vacuo
  11. customThis solid is crystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-d0778592d6834b869499492f2e68643a
Source dataset
uspto-grants-1994_05
Patent number
US05308853

Reaction notes

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