Thiophenol → Ethyl 2-phenylsulfanyl-thiazole-5-carboxylate

HRID 2298359Notes

Reaction equation

HRID 2298359 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][CH:7]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([S:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 10901519Ethyl 2-phenylsulfanyl-thiazole-5-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-bromo-1,3-thiazole-5-carboxylic acid ethyl ester (1.5 g, 6.15 mmol, 1 eq) and K2CO3 (1.7 g, 12.3 mmol, 2 eq) in EtOH (60 mL) is cooled in an ice bath, and thiophenol (0.631 mL, 6.15 mmol, 1 eq) is added. The reaction is monitored by HPLC until the starting material is consumed. The reaction mixture is filtered (to remove a solid by-product), and the solvent is removed in vacuo. The crude mixture is purified by silica gel chromatography using a Biotage Flash 40S column using 2% EtOAc in hexanes to afford the product as an oil (0.784 g, 46%). MS (ESI) for C12H11NO2S2m/z 266.1 (M+H)+.

Workup

  1. temperatureis cooled in an ice bath
  2. customis consumed
  3. filtrationThe reaction mixture is filtered (
  4. customto remove a solid by-product), and the solvent
  5. customis removed in vacuo
  6. customThe crude mixture is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a30e3ab6e8c841d6ba24668fe2cdf3d3
Source dataset
uspto-grants-2002_12
Patent number
US06492385B2

Reaction notes

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