Sodium Iodide → 5-Chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole

HRID 346491

反応式

HRID 346491 の反応式
[Na+].[I-].[Cl:3][C:4]1[S:8][N:7]=[C:6]([CH2:9]Cl)[N:5]=1.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.CCOC(C)=O.O>[Cl:3][C:4]1[S:8][N:7]=[C:6]([CH2:9][S:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 7969ThiophenolHCID 10340Sodium CarbonateHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazole

生成物 1

HCID 210814585-Chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1.05 eq of NaI were dissolved in dry acetone. 1 eq of 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole, 1.03 eq of the thiophenol and 1 eq of Na2CO3 were added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with EtOAc and water. The organic phase was washed with an aqueous solution of Na2SO3 (sat), dried over MgSO4 and evaporated in vacuo. Preparative HPLC purification gave the 5-chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole. This was subsequently dissolved in 95% ethanol and conc. NH3 (aq) was added. In some cases acetonitrile was added in order to completely dissolve the starting material. The mixture was transferred to a microwave tube and run in the microwave at 150° C. for 5 min. the reaction was quenched with water and the desired 3-arylthiomethyl-5-amino-1,2,4-thiadiazole worked up and purified using standard procedures.

後処理

  1. washThe organic phase was washed with an aqueous solution of Na2SO3 (sat)
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customPreparative HPLC purification

出典と根拠

ORDレコード
ord-111ed844a99d4345a191b2cd24b48c9b
出典データセット
uspto-grants-2007_02
特許番号
US07173030B2

関連ノート

読み込み中…