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

HRID 1359647Notes

Reaction equation

HRID 1359647 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 (ESI) 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-7eecb3045b2245dd89d6bbfc0023f821
Source dataset
uspto-grants-2003_07
Patent number
US06599916B2

Reaction notes

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