Sodium hydride → HCID 20034621, Verbindung

HRID 231161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231161
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:9][C:10]2[NH:14][C:13]3=[CH:15][S:16][CH:17]=[C:12]3[N:11]=2)=[N:6][CH:7]=1.[H-].[Na+].[C:20](=O)([O:31]C1C=CC=CC=1)[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>CN(C=O)C>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][O:21][C:20]([N:11]2[C:12]3=[CH:17][S:16][CH:15]=[C:13]3[N:14]=[C:10]2[S:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)=[O:31])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3084543p-Methoxybenzyl phenyl carbonateHCID 14014797HCID 14014797, Verbindung

Produkt 1

HCID 20034621HCID 20034621, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 1.3 g (5 mmol) of 2-(5-methyl-2-picolylmercapto)-1H-thieno[3,4-d]imidazole dissolved in 15 ml of anhydrous DMF were added, under nitrogen, 275 mg (6 mmol) of sodium hydride. After the mixture had been heated at 40°-50° C. for 10 min, at room temperature 1.92 g (7.5 mmol) of 4-methoxybenzyl phenyl carbonate (prepared from 4-methoxybenzyl alcohol and phenyl chloroformate) were added, and the mixture was heated at 30°-40° C. for 10 minutes and stirred at room temperature for 1 hour. The solvent was removed by distillation in vacuo, and water was added to the residue. The oily/resinous precipitate was taken up in CH2Cl2, and the solution was dried over MgSO4 and the solvent was evaporated off. The residue crystallized from diethyl ether and was recrystallized from isopropanol. Melting point 120°-121° C.

Aufarbeitung

  1. additionwere added, under nitrogen
  2. additionwere added
  3. temperaturethe mixture was heated at 30°-40° C. for 10 minutes
  4. customThe solvent was removed by distillation in vacuo, and water
  5. additionwas added to the residue
  6. dry with materialthe solution was dried over MgSO4
  7. customthe solvent was evaporated off
  8. customThe residue crystallized from diethyl ether
  9. customwas recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-449e5f0954f844debd26d10124aef7b7
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845118

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