Ethanol → HCID 13754329, compound

HRID 980205Notes

Reaction equation

HRID 980205 reaction equation
Cl[C:2]1[CH:6]([N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])[CH2:5][O:4][N:3]=1.[C:18]1(C)[C:23]([SH:24])=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:26](O)C>C(N(CC)CC)C>[C:20]1([CH3:26])[CH:19]=[CH:18][C:23]([S:24][C:2]2[CH:6]([N:7]3[C:11](=[O:12])[C:10]4=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]4[C:8]3=[O:17])[CH2:5][O:4][N:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 87122-ThiocresolHCID 9837847HCID 9837847, compound

Product 1

HCID 13754329HCID 13754329, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-Chloro-4-phthalimido-4,5-dihydroisoxazole (2.0 g, 8 mmol) was dissolved in 50 ml of ethanol (3A grade) and cooled to 0°-5° C. on ice bath. A solution of thiocresol (1.0 g, 8 mmol) in 30 ml of triethylamine was added to the first solution. The reaction mixture was stirred at room temperature for 4 hours. The reaction product was purified by flash chromatography on silica gel (230-400 mesh), eluted with 2:1 petroleum ether/ethyl acetate and collected in 20 ml fractions. Unreacted thiocresol eluted in fractions 2-6, and the reaction product 3-(p-tolylthio)-4-phthalimido-4,5-dihydroisoxazole (1.65 g, 60.95%) was eluted in fractions 8-32.

Workup

  1. temperaturecooled to 0°-5° C. on ice bath
  2. customThe reaction product was purified by flash chromatography on silica gel (230-400 mesh)
  3. washeluted with 2:1 petroleum ether/ethyl acetate
  4. customcollected in 20 ml fractions
  5. washUnreacted thiocresol eluted in fractions 2-6
  6. washthe reaction product 3-(p-tolylthio)-4-phthalimido-4,5-dihydroisoxazole (1.65 g, 60.95%) was eluted in fractions 8-32

Sources & evidence

ORD record
ord-1920c1dd16ab4c629dcfaea23f9dc1fd
Source dataset
uspto-grants-1987_01
Patent number
US04636517

Reaction notes

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