Sodium → HCID 178443738, compound

HRID 1491513Notes

Reaction equation

HRID 1491513 reaction equation
[CH2:1]([O:9][C:10](=[CH:13]N(C)C)[CH:11]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.Cl.[C@H:19]1([C:28]([NH2:30])=[NH:29])[CH2:24][CH2:23][C@H:22]([C:25]([NH2:27])=[NH:26])[CH2:21][CH2:20]1.[Na]>C(O)C>[CH2:1]([O:9][C:10]1[CH:11]=[N:26][C:25]([C@H:22]2[CH2:21][CH2:20][C@H:19]([C:28]3[N:30]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:13][N:29]=3)[CH2:24][CH2:23]2)=[N:27][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 53649216HCID 53649216, compoundHCID 178478781HCID 178478781, compound

Product 1

HCID 178443738HCID 178443738, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.27 g (9.96 mmol) of 2-octyloxy-3-dimethylaminoacrolein in 5 ml of ethanol and 1.0 g (4.15 mmol) of transcyclohexane-1,4-diamidine dihydrochloride are added dropwise at room temperature to 230 mg (9.96 mmol) of sodium, dissolved in 6.3 ml of ethanol, and the mixture is refluxed for 120 hours. After cooling, the reaction solution is adjusted to pH 3 using semiconcentrated HC1 and evaporated, and 30 ml of water are added to the residue. The aqueous solution is extracted several times with dichloromethane. The organic phases are combined, dried over magnesium sulfate and evaporated in vacuo. Chromatographic purification on silica gel and crystallization from hexane gives 380 mg (18%) of the end product. The product has the following phase sequence:

Workup

  1. temperaturethe mixture is refluxed for 120 hours
  2. temperatureAfter cooling
  3. customevaporated
  4. addition30 ml of water are added to the residue
  5. extractionThe aqueous solution is extracted several times with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customChromatographic purification
  9. customon silica gel and crystallization from hexane

Sources & evidence

ORD record
ord-6d5ce8c917ee447a95753e8a4bced500
Source dataset
uspto-grants-1994_12
Patent number
US05370823

Reaction notes

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