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

HRID 1359647노트

반응식

HRID 1359647 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-7eecb3045b2245dd89d6bbfc0023f821
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599916B2

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