Phosgene → (3-tert-Butyl-isoxazol-5-yl)-thiocarbamic acid S-(4-methoxy-phenyl)ester

HRID 2354043Notes

Reaction equation

HRID 2354043 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].C(Cl)(Cl)=O.[C:20]([C:24]1[CH:28]=[C:27]([NH2:29])[O:26][N:25]=1)([CH3:23])([CH3:22])[CH3:21]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10](=[O:13])[NH:29][C:27]2[O:26][N:25]=[C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:28]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 20956943-Tert-butyl-1,2-oxazol-5-amine

Product 1

HCID 59380989(3-tert-Butyl-isoxazol-5-yl)-thiocarbamic acid S-(4-methoxy-phenyl)ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-Methoxy-benzenethiol (0.20 g, 1 eq) and potassium carbonate (0.47 g, 2.5 eq) in dry THF was allowed to stir at room temperature under argon for an hour. Then the stirred suspension was cooled to 0° C. and to it was added drop wise a solution of phosgene (0.17 g 1.2 eq). The reaction stirred at 0° C. for half an hour. Then 3-tert-Butyl-isoxazol-5-ylamine (0.20 g, 1 eq) in THF was added dropwise. The reaction was allowed to warm to room temperature and stirred overnight. The solvent was removed and extracted with ethyl acetate and water. The organic layer was dried over magnesium sulfate and solvent removed. It was purified by HPLC. Yield: 157 mg (36%), LC/MS [MH+] 307.

Workup

  1. temperatureThen the stirred suspension was cooled to 0° C. and to it
  2. stirringThe reaction stirred at 0° C. for half an hour
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. customThe solvent was removed
  6. extractionextracted with ethyl acetate and water
  7. dry with materialThe organic layer was dried over magnesium sulfate and solvent
  8. customremoved
  9. customIt was purified by HPLC

Sources & evidence

ORD record
ord-6bc5fc69a51641c1b8e14ebe6c75d733
Source dataset
uspto-grants-2010_07
Patent number
US07750160B2

Reaction notes

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