Sodium Methoxide → 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

HRID 35451Notes

Reaction equation

HRID 35451 reaction equation
[CH3:1][C:2]1([CH3:29])[C:13]2[C:5](=[CH:6][C:7]3[NH:8][C:9]([S:14][CH2:15][C:16]4[C:21]([CH3:22])=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=4)=[N:10][C:11]=3[CH:12]=2)[C:4]([CH3:27])([CH3:26])[C:3]1=[O:28].[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:15][S:14][C:9]2[NH:8][C:7]3[CH:6]=[C:5]4[C:13](=[CH:12][C:11]=3[N:10]=2)[C:2]([CH3:29])([CH3:1])[C:3](=[O:28])[C:4]4([CH3:27])[CH3:26])[C:21]=1[CH3:22]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 221514395,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

Product 1

HCID 98654732-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.4 g (0.011 mol) of 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl -4-nitro-2-pyridyl)methyl)thio]indeno[5,6-d]imidazol-6(1H)-one in 100 ml of abs. methanol is treated with 3 g of sodium methylate, whereupon the mixture is boiled at reflux for 18 houre under argon. After concentrating the reaction mixture in vacuo the residue is treated with methylene chloride, whereupon the mixture is buffered by means of glacial acetic acid; the methylene chloride phase is extracted several times with a sodium bicarbonate solution, dried and evaporated. By recrystallisation from ethyl acetate there is obtained 5,7-dihydro-2-[[(4-methoxy-3 -methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one of melting point 222°-226°.

Workup

  1. temperatureat reflux for 18 houre under argon
  2. concentrationAfter concentrating the reaction mixture in vacuo the residue
  3. additionis treated with methylene chloride, whereupon the mixture
  4. extractionthe methylene chloride phase is extracted several times with a sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customBy recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-3e5f115cd4dd48d3ae45ef8a0d1e2cb6
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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