N-Iodosuccinimide → HCID 59208476, compound

HRID 2243073Notes

Reaction equation

HRID 2243073 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]>CCOC(C)=O.CO>[NH2:25][C:23]1[S:24][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:11]2[N:10]([CH3:9])[CH:14]=[CH:13][N:12]=2)[N:22]=1

Participants

6

Reactant 3

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

Product 1

HCID 59208476HCID 59208476, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

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 63) 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 addition of 4.7 g (62 mmol) thiourea. The mixture was heated at reflux for 1 hour, then the 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 the title compound: MS (ES) (M+H)+: 239 for C9H10N4O2S; NMR: 3.48 (s, 3H), 3.57 (s, 3H), 6.90 (s, 1H), 7.12 (s, 1H), 7.98 (s, 2H).

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. temperatureThe mixture was heated
  8. temperatureat reflux for 1 hour
  9. customthe solvent was removed
  10. filtrationInsoluble material was collected by filtration
  11. washrinsed well with water
  12. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-bcc0ebdece1c47acac24508df8ba6fe1
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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