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

HRID 703155Notes

Reaction equation

HRID 703155 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 of 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)met hyl]thio]indeno[5,6-d]imidazol-6(lH)-one in 100 ml of absolute methanol was treated with 3 g of sodium methylate, whereupon the mixture was boiled at reflux for 18 hours under argon. After concentrating the reaction mixture in vacuo the residue was treated with methylene chloride whereupon the mixture was buffered by means of glacial acetic acid; the methylene chloride phase was extracted several times with a sodium bicarbonate solution, dried and evaporated. By recrystallisation from ethyl acetate there was obtained 5,7-dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d ]imidazol-6(lH)-one of melting point 222-226°.

Workup

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

Sources & evidence

ORD record
ord-922ccdb4b814429cafddab210f39e175
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

Loading…