Nitrogen → 4-(3-Bromo-phenylsulfanylmethyl)-2-phenyl-thiazole

HRID 1717115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717115
[H-].[Na+].N#N.[Br:5][C:6]1[CH:7]=[C:8]([SH:12])[CH:9]=[CH:10][CH:11]=1.Cl[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:18][CH:19]=1>C1COCC1>[Br:5][C:6]1[CH:7]=[C:8]([S:12][CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[S:18][CH:19]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 80597m-BromobenzenethiolHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazole

Produkt 1

HCID 596546084-(3-Bromo-phenylsulfanylmethyl)-2-phenyl-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (53 mg, 2.2 mmol) was suspended in dry THF (1.5 ml) under a stream of N2 and 3-bromo-benzenethiol (378 mg, 2 mmol) was added dropwise to the suspension over 5 min. 4-Chloromethyl-2-phenyl-thiazole (419 mg, 2 mmol) was added and the solution left stirring overnight. The reaction mixture was quenched with a saturated K2CO3 solution (8 ml) and extracted with EtOAc (3×4 ml). The combined organic layers were washed with saturated K2CO3 solution (4 ml), dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography eluting with 20% EtOAc in heptane to give the title compound.

Aufarbeitung

  1. additionwas added dropwise to the suspension over 5 min
  2. waitthe solution left
  3. customThe reaction mixture was quenched with a saturated K2CO3 solution (8 ml)
  4. extractionextracted with EtOAc (3×4 ml)
  5. washThe combined organic layers were washed with saturated K2CO3 solution (4 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluting with 20% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-3ac0b3bda27b4691ae7e5cc1ccf33c51
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803841B2

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