Potassium Carbonate → HCID 11148479, compound

HRID 990571Notes

Reaction equation

HRID 990571 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:7]=1OCC(N)=O)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C[N:27]1CCCC1=O>C(OCC)(=O)C>[C:1]([NH:4][CH2:5][C:6]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:7]=1[NH2:27])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 11817999HCID 11817999, compound

Product 1

HCID 11148479HCID 11148479, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

120 g of the 2-(N-acetylaminomethyl)-4-nitrophenoxyacetamide made in step 1 are dissolved in 450 ml of N-methylpyrrolidone, mixed with 155 g of potassium carbonate and heated for 4.5 hours at 100° C. Subsequently the reaction mixture is cooled to room temperature, diluted with 840 ml of ethyl acetate, filtered and the solvent is evaporated in vacuum at 60 to 80° C. The remaining residue is crystallized by addition of ethanol. The product is filtered with suction, taken up in 250 ml ethanol and heated briefly under reflux. Subsequently the solution is cooled, filtered and the residue is dried in vacuum. 46.6 g of a yellow powder are obtained with a melting point of 208 to 210° C.

Workup

  1. temperatureSubsequently the reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. customthe solvent is evaporated in vacuum at 60 to 80° C
  4. customThe remaining residue is crystallized by addition of ethanol
  5. filtrationThe product is filtered with suction
  6. temperatureheated briefly
  7. temperatureunder reflux
  8. temperatureSubsequently the solution is cooled
  9. filtrationfiltered
  10. customthe residue is dried in vacuum

Sources & evidence

ORD record
ord-818602e58f7641eb8ed12a0bbce3ce53
Source dataset
uspto-grants-2002_10
Patent number
US06461390B1

Reaction notes

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