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

HRID 1444333Notes

Reaction equation

HRID 1444333 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0663b778deaf40fb8b34e07164706c1e
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

Loading…