Sodium Methoxide → HCID 18961504, compound

HRID 1707539Notes

Reaction equation

HRID 1707539 reaction equation
Cl.[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([C:19](=[NH:21])[NH2:20])=[CH:15][CH:16]=2)[C:11]1=[O:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C[O-].[Na+]>CO>[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([C:19]3[N:20]=[CH:13][C:12]([CH2:11][CH2:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:17][N:21]=3)=[CH:15][CH:16]=2)[C:11]1=[O:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18961515HCID 18961515, compound

Product 1

HCID 18961504HCID 18961504, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g (3.1 mM) of 2-octyl-6-amidino-1-indanone hydrochloride, 0.38 g (7.0 mM) of sodium methylate, 0.78 g (3.26 mM) of α-decyl-β-dimethylaminoacrolein and 10 ml of methanol were placed in a 10 ml-round bottomed flask, followed by refluxing for 17 hours under stirring. After the reaction, the reaction mixture was cooled on an ice water bath to precipitate a crystal. The crystal was recovered by filtration and purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1), followed by recrystallization from a mixture solvent (toluene/methanol) to obtain 0.59 g of 2-octyl-6-(5-decylpyrimidine-2-yl)-1-indanone (Yield: 41%, m.p.=83° C.).

Workup

  1. temperatureby refluxing for 17 hours
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled on an ice water bath
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. custompurified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  7. customfollowed by recrystallization from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-02b06696275f492d94a39ab5ba3a1574
Source dataset
uspto-grants-1994_10
Patent number
US05354501

Reaction notes

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