Sodium Carbonate → 2-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]5,7-dihydro-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

HRID 979845Notes

Reaction equation

HRID 979845 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH3:11][C:12]1([CH3:39])[C:23]2[C:15](=[CH:16][C:17]3[NH:18][C:19]([S:24][CH2:25][C:26]4[C:31]([CH3:32])=[C:30]([N+]([O-])=O)[CH:29]=[CH:28][N:27]=4)=[N:20][C:21]=3[CH:22]=2)[C:14]([CH3:37])([CH3:36])[C:13]1=[O:38]>C(O)C>[CH2:2]([O:3][C:30]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:25][S:24][C:19]2[NH:18][C:17]3[CH:16]=[C:15]4[C:23](=[CH:22][C:21]=3[N:20]=2)[C:12]([CH3:11])([CH3:39])[C:13](=[O:38])[C:14]4([CH3:37])[CH3:36])[C:31]=1[CH3:32])[CH3:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2723922Sodium ethoxideHCID 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 221514652-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]5,7-dihydro-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.5 g of sodium ethylate, 20 g of sodium carbonate and 400 ml of ethanol was stirred at 50° under argon for 30 minutes and then treated with 7 g 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. After stirring at 50° for 5 hours under argon the reaction mixture was concentrated in vacuo. The residue was treated with methylene chloride and buffered by means of glacial acetic acid; the methylene chloride solution was extracted with sodium bicarbonate solution, dried and concentrated. The residue was chromatographed on silica gel while eluting with methylene chloride/ethyl acetate (3:1), the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. There was obtained 2-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]5,7-dihydro-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one which melts at 175°-176° after recrystallization from ether.

Workup

  1. stirringAfter stirring at 50° for 5 hours under argon the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was treated with methylene chloride
  4. extractionthe methylene chloride solution was extracted with sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. washwhile eluting with methylene chloride/ethyl acetate (3:1)
  9. customthe pressure being produced with nitrogen gas

Sources & evidence

ORD record
ord-32d66918992f46ae8b5a06dac5ae3f99
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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