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

HRID 1638297노트

반응식

HRID 1638297 반응식
[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

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 132544871-(2-Bromoethoxy)-4-phenoxybenzeneHCID 178418361HCID 178418361, 화합물HCID 178527880HCID 178527880, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ded7ebaf1e84654a50f3737d37c676e
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04879292

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