Potassium Carbonate → HCID 18696217, compound

HRID 1739061Notes

Reaction equation

HRID 1739061 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.C(OC([NH:19][CH2:20][CH2:21][SH:22])=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:1].[NH2:19][CH2:20][CH2:21][S:22][C:2]1[C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 154539733-Chloro-5-fluoro-1,2-benzoxazole

Product 1

HCID 18696217HCID 18696217, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-5-fluoro-1,2-benzisoxazole (0.83 g) in dimethylformamide (8 ml) was added 2-t-butoxycarbonylaminoethanethiol (0.86 g) and potassium carbonate (0.67 g) with stirring under nitrogen atmosphere, and the mixture was then stirred at 80° C. for 3 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and the combined extracts were washed with brine and dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography, to give the title compound (1.21 g, 80%) as a colorless powder.

Workup

  1. stirringthe mixture was then stirred at 80° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8022e1e42d54258973193149ad589f1
Source dataset
uspto-grants-1999_10
Patent number
US05965591

Reaction notes

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