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Potassium Carbonate → 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

HRID 35450
Notes
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Reaction equation

HRID 35450 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][N:4]=1.[SH:13][C:14]1[NH:18][C:17]2[CH:19]=[C:20]3[C:24](=[CH:25][C:16]=2[N:15]=1)[C:23]([CH3:27])([CH3:26])[C:22](=[O:28])[C:21]3([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:29][C:21]1([CH3:30])[C:20]2[C:24](=[CH:25][C:16]3[NH:15][C:14]([S:13][CH2:2][C:3]4[C:8]([CH3:9])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][N:4]=4)=[N:18][C:17]=3[CH:19]=2)[C:23]([CH3:27])([CH3:26])[C:22]1=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 160959042-(Chloromethyl)-3-methyl-4-nitropyridineHCID 178429018HCID 178429018, compound

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 180Acetone
Solvent

Procedure

A solution of 11,5 g (0.062 mol) of 2-chloromethyl-3 -methyl-4-nitropyridine and 16 g (0.06 mol) of 5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno[5,6-d]-imidazol-6(1H)-one in 200 ml of abs. acetone is treated with 13 g of finely ground potassium carbonate and the mixture is stirred at room temperature under argon for 18 hours, 100 ml of acetone are distilled off in vacuo, whereupon the residue is poured on to ice. The product which crystallizes out is filtered off and dissolved in methylene chloride; the solution obtained is washed with water, dried and concentrated. By recrystallization from ethyl acetate/ether there is obtained 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 of melting point 181°-183° (decomposition).

Workup

  1. distillation100 ml of acetone are distilled off in vacuo, whereupon the residue
  2. additionis poured on to ice
  3. customThe product which crystallizes out
  4. filtrationis filtered off
  5. dissolutiondissolved in methylene chloride
  6. customthe solution obtained
  7. washis washed with water
  8. customdried
  9. concentrationconcentrated
  10. customBy recrystallization from ethyl acetate/ether there

Sources & evidence

ORD record
ord-290a559b7d5e464db1ce918e68b2764b
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766133

Reaction notes

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