Benzyl mercaptan → 2-(Benzylthio)-5-bromopyrimidine

HRID 905220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905220
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1>CC[O-].[Na+]>[CH2:1]([S:8][C:10]1[N:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7509Benzyl mercaptanHCID 6066655-Bromo-2-chloropyrimidine

Produkt 1

HCID 204757122-(Benzylthio)-5-bromopyrimidineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2723922Sodium ethoxideLösungsmittel

Versuchsvorschrift

Benzyl thiol (22 mmol) was added to 0.146 M ethanolic NaOEt (150 ml) at room temperature followed by 2-chloro-5-bromopyrimidine (20 mmol). The mixture was stirred at room temperature for 70 min, heated under reflux for 40 min, the solvent evaporated off at reduced pressure, the residue extracted with chloroform (100 ml), the chloroform solution washed with 2 M NaOH, and the dried (MgSO4) solution evaporated; yield 81%, m.p. 68°-69° C. (dil. MeOH). 1H NMR (CDCl3): δ4.36 (CH2), 7.26 (Ph), 8.50. (H-4, H-6).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 40 min
  3. customthe solvent evaporated off at reduced pressure
  4. extractionthe residue extracted with chloroform (100 ml)
  5. washthe chloroform solution washed with 2 M NaOH
  6. dry with materialthe dried (MgSO4) solution
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f5eec3961e484c66a0c6179918ee6957
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04423047

Notizen zur Reaktion

Wird geladen…