Sodium Methoxide → HCID 54042082, compound

HRID 1770154Notes

Reaction equation

HRID 1770154 reaction equation
Cl.[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19](=[NH:21])[NH2:20])[CH:16]=2)[CH2:11]1)[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][CH:14]=[C:15]([C:19]3[N:20]=[CH:11][C:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:18][N:21]=3)[CH:16]=2)[CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20095057HCID 20095057, compound

Product 1

HCID 54042082HCID 54042082, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.80 g (2.59 mM) of 2-octyl-5-amidinoindan hydrochloride, 0.30 g (5.55 mM) of sodium methylate, 0.62 g (2.73 mM) of α-octyloxy-β-dimethylaminoacrolein and 12 ml of methanol were placed in a 30 ml-round bottomed flask, followed by refluxing for 18 hours and 20 minutes 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), followed by recrystallization from a mixture solvent (acetone/methanol) to obtain 0.57 g of 2-octyl-5-(5-octylpyrimidine-2-yl) indan (Yield: 50.4%). ##STR133##

Workup

  1. temperatureby refluxing for 18 hours and 20 minutes
  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)
  7. customfollowed by recrystallization from a mixture solvent (acetone/methanol)

Sources & evidence

ORD record
ord-3973910c6c67487ba60629d62f9c0794
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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