Thiophenol → 5-Phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

HRID 2301874Notes

Reaction equation

HRID 2301874 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Cl)=[N:9][N:10]=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>CC#N>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:9][N:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 12348753Ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 699746815-Phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid ethyl esterYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloro-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester (1.0 g, 5.2 mmol, 1 eq), and K2CO3 (1.44 g, 104 mmol, 2 eq) in CH3CN (50 mL), thiophenol (0.53 mL, 5.2 mmol, 1 eq) is added. The reaction is stirred overnight at room temperature. The reaction is filtered to remove the salts, and the filtrate is washed with CH3CN. The solvents are removed under reduced pressure, and the product is recrystallized from EtOH to give 5-phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester (1.03 g, 74%). MS (ESD for C11H10N2O2S2 m/z 267.0 (M+H)+.

Workup

  1. filtrationThe reaction is filtered
  2. customto remove the salts
  3. washthe filtrate is washed with CH3CN
  4. customThe solvents are removed under reduced pressure
  5. customthe product is recrystallized from EtOH

Sources & evidence

ORD record
ord-e0495d5931a941a6b396567f8016698b
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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