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

HRID 979864
Notes
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Reaction equation

HRID 979864 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]3[C:12](=[CH:13][C:4]=2[N:3]=1)[C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[C:9]3([CH3:18])[CH3:17].Cl.Cl[CH2:21][C:22]1[C:27]([CH3:28])=[C:26]([O:29][CH2:30][CH3:31])[C:25]([CH3:32])=[CH:24][N:23]=1.[OH-].[Na+]>O>[CH2:30]([O:29][C:26]1[C:25]([CH3:32])=[CH:24][N:23]=[C:22]([CH2:21][S:1][C:2]2[NH:3][C:4]3[CH:13]=[C:12]4[C:8](=[CH:7][C:5]=3[N:6]=2)[C:9]([CH3:18])([CH3:17])[C:10](=[O:16])[C:11]4([CH3:14])[CH3:15])[C:27]=1[CH3:28])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 221514582-Chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochlorideHCID 178429018HCID 178429018, compound

Product 1

HCID 221514715,7-dihydro-2-[[(4-ethoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

7.8 g of 5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one were suspended in 200 ml of alcohol and treated while cooling with ice with 7.1 g of 2-chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochloride. Thereafter, a solution of 2.4 g of sodium hydroxide in 100 ml of water was added dropwise thereto, the mixture was left to boil at reflux overnight and subsequently evaporated to dryness in vacuo. The residue was dissolved in 500 ml of methylene chloride. The solution was washed firstly with 250 ml of 1.5N sodium hydroxide solution and then with 3×250 ml of water, dried over sodium sulfate and evaporated in vacuo. The product was purified on 150 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent. Crystallization from methylene chloride/petroleum ether gave 5,7-dihydro-2-[[(4-ethoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one of melting point 179°-180°.

Workup

  1. additiontreated
  2. waitthe mixture was left
  3. temperatureat reflux overnight
  4. customsubsequently evaporated to dryness in vacuo
  5. dissolutionThe residue was dissolved in 500 ml of methylene chloride
  6. washThe solution was washed firstly with 250 ml of 1.5N sodium hydroxide solution
  7. dry with materialwith 3×250 ml of water, dried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe product was purified on 150 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent
  10. customCrystallization from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-a69a9e5944f3402fbb67e4f22c1b5710
Source dataset
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04634710

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes