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

HRID 2301874ノート

反応式

HRID 2301874 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-e0495d5931a941a6b396567f8016698b
出典データセット
uspto-grants-2002_12
特許番号
US06500840B2

反応ノート

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