Ethyl Acetate → HCID 59208395, compound

HRID 655749Notes

Reaction equation

HRID 655749 reaction equation
IN1C(=O)CCC1=O.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18].[NH2:22][C:23]([NH2:25])=[S:24].C[CH2:27][O:28][C:29](C)=O>>[NH2:22][C:23]1[S:24][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:11]2[N:10]([CH2:9][CH2:27][O:28][CH3:29])[CH:14]=[CH:13][N:12]=2)[N:25]=1

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 2723790ThioureaHCID 20029381Methyl 1-methyl-β-oxo-1H-imidazole-2-propanoate2×

Product 1

HCID 59208395HCID 59208395, compound

Procedure

N-Iodosuccinimide (9.3 g, 41 mmol) was added to a mixture of 7.52 g (41 mmol) methyl 3-(1-methyl-1H-imidazol-2-yl)-3-oxopropanoate (Intermediate 10) and 7.5 g Amberlyst-15 resin in 400 ml EtOAc followed by stirring for 1 hour at room temperature. The resin was filtered off and rinsed with EtOAc. Solvent was removed from the filtrate and the residue was taken up in diethyl ether. Insoluble material was filtered off and rinsed with additional ether. Solvent was removed from the filtrate and the residue was dissolved in 200 ml MeOH before added 4.7 g (62 mmol) thiourea. The mixture was heated at reflux for 1 hour. Solvent was removed and the residue was taken up in aqueous Na2CO3. Insoluble material was collected by filtration and rinsed well with water. The solids were dried in vacuo affording 4.51 g of product: MS (ES) (M+H)+: 283 for C11H14N4O3S

Workup

  1. filtrationThe resin was filtered off
  2. washrinsed with EtOAc
  3. customSolvent was removed from the filtrate
  4. filtrationInsoluble material was filtered off
  5. washrinsed with additional ether
  6. customSolvent was removed from the filtrate
  7. dissolutionthe residue was dissolved in 200 ml MeOH
  8. temperatureThe mixture was heated
  9. temperatureat reflux for 1 hour
  10. customSolvent was removed
  11. filtrationInsoluble material was collected by filtration
  12. washrinsed well with water
  13. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-07b44fc3b42740b8bbab87056c7f9e91
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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