Sodium Methoxide → HCID 70347307, compound

HRID 582599Notes

Reaction equation

HRID 582599 reaction equation
Cl.[C:2]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[NH:4])[NH2:3].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:37])[C:23](=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=1)[C:24](=O)[CH3:25].C[O-].[Na+]>C(O)C>[NH2:4][C:2]1[NH:3][C:24]([CH3:25])=[C:23]([C:22](=[O:37])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 15555354Ethyl 2-carbamimidoylacetate hydrochlorideHCID 54129570HCID 54129570, compound

Product 1

HCID 70347307HCID 70347307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.7 g of ethyl amidinoacetate hydrochloride and 33.4 g of 14-bromo-3-(3-nitrobenzylidene)tetradecane-2,4-dione are dissolved in 300 ml of ethanol and the solution is treated with 14.5 ml of a 5.25M of sodium methoxide solution. The mixture is heated to boiling under reflux for 7 h and then concentrated in vacuo. The residue is dissolved in ethyl acetate and the solution is washed with water, dried over sodium sulfate, filtered and concentrated again. The oily residue is dried in vacuo and reacted in the next stage without further purification.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 7 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated again
  9. customThe oily residue is dried in vacuo
  10. customreacted in the next stage without further purification

Sources & evidence

ORD record
ord-8718411bda0345a783dbcc411c4163b6
Source dataset
uspto-grants-1999_07
Patent number
US05925642

Reaction notes

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