Ethyl benzoylacetate → HCID 178494249, compound

HRID 1429123Notes

Reaction equation

HRID 1429123 reaction equation
[Na].S(O)(O)(=O)=O.[CH3:7][O:8][C:9](=[NH:11])[NH2:10].[C:12]([CH2:20][C:21](OCC)=[O:22])(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH3:7][O:8][C:9]1[N:10]=[C:21]([OH:22])[CH:20]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:11]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 5360545Sodium

Product 1

HCID 178494249HCID 178494249, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

Sodium (4.14 g, 180 mmol) was dissolved in dry methanol (120 ml) and the solution was cooled to 0-5° C. O-Methylisourea sulfat (10.3 g, 60 mmol) and ethyl benzoylacetate (11.5 g, 60 mmol) was added and the mixture was stirred for two hours at room temperature and then refluxed for twelve hours. The mixture was evaporated, acidified with 2M HCl and extracted three tines with ethyl acetate and three times with DCM. The organic phase was dried and evaporated and the residue was suspended in diethyl ether, the solid filtered off, washed and dried which gave the title compound, (1.0 g) MS+1=203.

Workup

  1. temperaturerefluxed for twelve hours
  2. customThe mixture was evaporated
  3. extractionextracted three tines with ethyl acetate and three times with DCM
  4. customThe organic phase was dried
  5. customevaporated
  6. filtrationthe solid filtered off
  7. washwashed
  8. customdried which

Sources & evidence

ORD record
ord-8bed296cec084a24aa9c9423c7168169
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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