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

HRID 703185Notes

Reaction equation

HRID 703185 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[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[C:25]([CH3:31])=[CH:24][N:23]=1.[OH-].[Na+]>O>[CH2:29]([O:28][C:26]1[C:25]([CH3:31])=[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])[CH:27]=1)[CH3:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 221514622-Chloromethyl-4-ethoxy-5-methylpyridine hydrochlorideHCID 178429018HCID 178429018, compound

Product 1

HCID 221514542-[[(4-ethoxy-5-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 962WaterSolvent

Procedure

6.1 g of 5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one were suspended in 100 ml of alcohol and treated while cooling with ice with 5.2 g of 2-chloromethyl-4-ethoxy-5-methylpyridine hydrochloride. Thereafter, a solution of 1.9 g of sodium hydroxide in 50 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 300 ml of methylene chloride. The solution was washed firstly with 200 ml of 1.5N sodium hydroxide solution and then with 3×200 ml of water, dried over sodium sulfate and evaporated in vacuo. The product was purified on 120 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent. Crystallization from methylene chloride/petroleum ether gave 2-[[(4-ethoxy-5-methyl-2pyridyl)methyl]thio]-5,7-dihydro-5,5,7,7-tetramethylindeno [5,6-d]imidazol-6(1H)- one of melting point 187°-189° .

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 300 ml of methylene chloride
  6. washThe solution was washed firstly with 200 ml of 1.5N sodium hydroxide solution
  7. dry with materialwith 3×200 ml of water, dried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe product was purified on 120 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-20275715b2d845fe8c773723af4c624d
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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