Sodium hydride → 2-[2-(4-Phenoxyphenoxy)ethylthio]-2-thiazoline

HRID 1073515ノート

反応式

HRID 1073515 の反応式
[H-].[Na+].[SH:3][C:4]1[S:5][CH2:6][CH2:7][N:8]=1.[H][H].[O:11]([C:18]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24]Br)=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[O:11]([C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][S:3][C:4]2[S:5][CH2:6][CH2:7][N:8]=2)=[CH:26][CH:27]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 132544871-(2-Bromoethoxy)-4-phenoxybenzeneHCID 178418361HCID 178418361、化合物HCID 178527880HCID 178527880、化合物

生成物 1

HCID 133867902-[2-(4-Phenoxyphenoxy)ethylthio]-2-thiazoline収率 66.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

To a suspension of sodium hydride (160 mg, 4.0 mmol; 60% in oil) in dimethylformamide (5 ml), a solution of 2-mercapto-2-thiazoline (476 mg, 4.0 mmol) in dimethylformamide (3 ml) was dropwise added with stirring, and stirring was continued until the generation of hydrogen gas ceased. To the resultant solution, there was dropwise added a solution of 2-(4-phenoxyphenoxy)ethyl bromide (1.17 g, 4.0 mmol) in dimethylformamide (3 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water (80 ml) and extracted with toluene (40 ml) three times. The toluene layer was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give 2-[2-(4-phenoxyphenoxy)ethylthio]-2-thiazoline (887 mg) as pale yellow crystals. M.P., 88.6° C.

後処理

  1. stirringstirring
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with toluene (40 ml) three times
  4. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3e5e278fcb7a4d6992a2f7204aa1397f
出典データセット
uspto-grants-1990_11
特許番号
US04970222

反応ノート

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