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

HRID 1638297Notes

Reaction equation

HRID 1638297 reaction equation
[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

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 132544871-(2-Bromoethoxy)-4-phenoxybenzeneHCID 178418361HCID 178418361, compoundHCID 178527880HCID 178527880, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1ded7ebaf1e84654a50f3737d37c676e
Source dataset
uspto-grants-1989_11
Patent number
US04879292

Reaction notes

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