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

HRID 979870
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 979870
[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][CH3:29])[C:25]([CH3:30])=[CH:24][N:23]=1.[OH-].[Na+]>O>[CH3:29][O:28][C:26]1[C:25]([CH3:30])=[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
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 221514312-(Chloromethyl)-4-methoxy-5-methylpyridine hydrochlorideHCID 178429018HCID 178429018, Verbindung

Produkt 1

HCID 202230585,7-dihydro-2-[[(4-methoxy-5-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

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 the suspension was treated while cooling with ice with 6.3 g of 2-chloromethyl-4-methoxy-5-methylpyridine hydrochloride. Thereafter, 2.4 g of sodium hydroxide in 100 ml of water were 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-methoxy-5-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one of melting point 204°-205°.

Aufarbeitung

  1. additionthe suspension was treated
  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

Quellen und Nachweise

ORD-Eintrag
ord-dc7da791a1df4980b44961455b47fb9c
Quelldatensatz
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04634710

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