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

HRID 2053237Notes

Reaction equation

HRID 2053237 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-66d888201372437db2bb5b61a891cfb9
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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