Thiophenol → HCID 18761606, compound

HRID 431796Notes

Reaction equation

HRID 431796 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([Sn](C)(C)C)[N:10]=1.[Br:15]C1SC=C(Br)N=1.C1(S)C=CC=CC=1.[OH-].[Na+]>C(O)C.O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([Br:15])[N:10]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 27632972,4-Dibromo-1,3-thiazoleHCID 18761618HCID 18761618, compound

Product 1

HCID 18761606HCID 18761606, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Synthesis of 2-Thiophenyl-4-(trimethylstannyl)thiazole 381 as illustrated in FIG. 53. 2,4-Dibromothiazole (358; 1.0 equiv) was dissolved in ethanol (0.1 M) and treated with thiophenol (3.0 equiv) and solid sodium hydroxide (3.0 equiv). The reaction mixture was heated at 45° C. for 4 h, upon which completion of the reaction was indicated by TLC. The mixture was poured into water and extracted with ether (2×). Drying (MgSO4) and evaporation of the solvents gave 2-thiophenyl-4-bromothiazole 380, which was isolated after flash column chromatography (silica gel, 5% EtOAc in hexanes) in 84% yield.

Workup

  1. extractionextracted with ether (2×)
  2. customDrying
  3. custom(MgSO4) and evaporation of the solvents

Sources & evidence

ORD record
ord-88c10ce57b974590a1924b471f19cde5
Source dataset
uspto-grants-2003_12
Patent number
US06660758B1

Reaction notes

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