5-chloro-3,4-diphenyl-1,2-oxazole → HCID 53801427, compound

HRID 343084Notes

Reaction equation

HRID 343084 reaction equation
Cl[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][S-:20].[Na+]>CS(C)=O.O>[CH3:19][S:20][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 2857785-chloro-3,4-diphenyl-1,2-oxazoleHCID 4378561Sodium methanethiolate

Product 1

HCID 53801427HCID 53801427, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-chloro-3,4-diphenylisoxazole (Step 1) (1.75 g, 6.84 mmol) in DMSO (30 mL) was added sodium thiomethoxide (0.58 g, 8.21 mmol). After stirring for 30 hours at room temperature, the reaction was diluted with water and extracted twice with Et2O . The combined ethereal phases were washed with NaHCO3 saturated solution, KHSO4 solution (0.25N), and brine, dried over MgSO4, filtered and concentrated in vacuo yielding 5-methylthio-3,4-diphenylisoxazole (1.53 g, 84%): mp 83°-86° C. 1H NMR (CDCl3 /300 MHz) 7.50-7.18 (m, 10H), 2.63 (s, 3H). FABLRMS m/z 268 (M+H). FABHRMS m/z 268.0781 (M+H C16H14NOS requires 268.0796). Anal. Calc'd for C16H13NOS: C, 71.88; H, 4.90; N, 5.24. Found: C, 71.71; H, 4.95; N, 5.17.

Workup

  1. extractionextracted twice with Et2O
  2. washThe combined ethereal phases were washed with NaHCO3 saturated solution, KHSO4 solution (0.25N), and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2424eca378a64928bcda2c1498ad51e9
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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