Sodium → HCID 13233232, compound

HRID 1731550Notes

Reaction equation

HRID 1731550 reaction equation
[Na].[N+:2]([C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[CH:8]=[C:9]([C:23]([CH3:25])=O)[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])([O-:4])=[O:3].Cl.[C:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(=[NH:32])[NH2:31]>C(O)C>[NH2:31][C:30]1[NH:32][C:23]([CH3:25])=[C:9]([C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])[CH:8]([C:7]2[CH:26]=[CH:27][CH:28]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)[C:33]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 15555354Ethyl 2-carbamimidoylacetate hydrochlorideHCID 54012662HCID 54012662, compound

Product 1

HCID 13233232HCID 13233232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1.15 g (50 mmol) of sodium in 100 ml of ethanol was added dropwise at room temperature, with stirring, to a solution of 18.8 g (50 mmol) of decyl 2-(3-nitrobenzylidene)acetoacetate and 8.3 g (50 mmol) of ethyl amidinoacetate hydrochloride in 250 ml of ethanol. The mixture was then heated to boiling for 15 minutes. After standing overnight, the precipitated sodium chloride was filtered off, the filtrate was evaporated in vacuo and the oily residue was brought to crystallization by trituration with ether/petroleum ether. The crude product was filtered off with suction and recrystallized from ethanol, melting point: 190°-191° C.

Workup

  1. temperatureThe mixture was then heated
  2. waitAfter standing overnight
  3. filtrationthe precipitated sodium chloride was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customthe oily residue was brought to crystallization by trituration with ether/petroleum ether
  6. filtrationThe crude product was filtered off with suction
  7. customrecrystallized from ethanol, melting point: 190°-191° C.

Sources & evidence

ORD record
ord-50d3648fe9e541e68eb13388d56dfd07
Source dataset
uspto-grants-1986_11
Patent number
US04622332

Reaction notes

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