Hydrochloric Acid → HCID 19919781, compound

HRID 1033117Notes

Reaction equation

HRID 1033117 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=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+].ICCCC.[ClH:50]>CN(C=O)C.CCOCC>[ClH:50].[CH2:1]([C:5]1[N:6]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)[C:7](/[CH:10]=[C:11]2\[N:12]([CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 10075811HCID 10075811, compound

Product 1

HCID 19919781HCID 19919781, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[[1-butyl-2,5-dioxo-3-(2-thienylmethyl)-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate (0.70 g, 1.46 mmol) in warm DMF (10 mL) is added K2CO3 (2.0 g, 15 mmol). After stirring for 5 minutes 1-iodobutane (0.312 g, 1.7 mmol) is added. The mixture is stirred for 2 hours. The mixture is filtered and the filtrate is concentrated in vacuo and treated with water (20 mL) to afford a gum upon decantation. This gum is dissolved in ether and washed with water and then dried over K2CO3. A viscous oil is obtained by evaporation of the solvents in vacuo. This oil is dissolved in ether and treated with ethereal HCl to precipitate a gum which is collected by decantation. This gum is dissolved in warm ethanol and ether is added to induce crystallization. The crystals are collected and washed with ether.

Workup

  1. additionis added
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. additiontreated with water (20 mL)
  5. customto afford a gum upon decantation
  6. washwashed with water
  7. dry with materialdried over K2CO3
  8. customA viscous oil is obtained by evaporation of the solvents in vacuo
  9. customto precipitate a gum which
  10. customis collected by decantation
  11. dissolutionThis gum is dissolved in warm ethanol
  12. additionether is added
  13. customcrystallization
  14. customThe crystals are collected
  15. washwashed with ether

Sources & evidence

ORD record
ord-544c9025eef141cc90dfc2e5142225b3
Source dataset
uspto-grants-1994_05
Patent number
US05308853

Reaction notes

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