Methanol → HCID 20095042, compound

HRID 1770156Notes

Reaction equation

HRID 1770156 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].[CH3:22][O-:23].[Na+].CO.S(=O)(=O)(O)O>O>[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[N:20]=[CH:18][C:17]([C:12]4[CH:13]=[CH:14][C:22]([OH:23])=[CH:10][CH:11]=4)=[CH:16][N:21]=3)[CH:16]=2)[CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 20095057HCID 20095057, compound

Product 1

HCID 20095042HCID 20095042, compoundYield 151.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.00 g (3.24 mM) of 2-octyl-5-amidinoindan hydrochloride, 0.70 g (13.7 mM) of sodium methylate, 1.04 g (3.26 mM) of 3-dimethylamino-2-(4-hydroxyphenyl)-N,N-dimethylpropene-(2)-ammonium perchlorate and 20 ml of methanol were placed in a 50 ml-round bottomed flask and heat-refluxed for 14.5 hours under stirring. After the reaction, an appropriate amount of water was poured into the reaction mixture and 0.66 ml of concentrated sulfuric acid was further added thereto under cooling with ice water, followed by stirring. The resultant insoluble matter was recovered by filtration, followed by washing with water and drying with anhydrous sodium sulfate. The resultant insoluble was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (acetone/methanol) to obtain 0.98 g of 2-octyl-5-[5-(4-hydroxyphenyl)pyrimidine-2-yl]indan (Yield: 75.6%).

Workup

  1. temperatureheat-refluxed for 14.5 hours
  2. customAfter the reaction
  3. additionwas further added
  4. stirringby stirring
  5. filtrationThe resultant insoluble matter was recovered by filtration
  6. washby washing with water
  7. dry with materialdrying with anhydrous sodium sulfate
  8. customThe resultant insoluble was purified by silica gel column chromatography (eluent: toluene)
  9. customrecrystallized from a mixture solvent (acetone/methanol)

Sources & evidence

ORD record
ord-ece9187d3b0244f09cf7c7d94ca50234
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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