Dimethylformamide → 6-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one

HRID 619739Notes

Reaction equation

HRID 619739 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([SH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.F[C:13]1[C:14]([N+:23]([O-:25])=[O:24])=[CH:15][C:16]2OC(=O)N[C:17]=2[CH:22]=1.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].C[N:33](C=O)C>>[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:13]3[C:14]([N+:23]([O-:25])=[O:24])=[CH:15][C:16]4[NH:33][C:26](=[O:29])[O:27][C:17]=4[CH:22]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110519635-IsoquinolinethiolHCID 112178355-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Product 1

HCID 218469496-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-oneYield 38%

Conditions

Temperature
130 °C

Procedure

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 20 ml, 5-fluoro-6-nitro-benzooxazolinone 670 mg (3.1 mmol) and potassium carbonate 1.29 g (9.3 mmol) were added, and the mixture was heated with stirring overnight at 130° C. The reaction mixture was concentrated under reduced pressure, acetone 20 ml was added to the residue, and insoluble materials were filtered. Chloroform 50 ml was added to the organic layer, the resulting precipitates were collected to give 6-(5-isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one 400 mg (38.0%).

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure, acetone 20 ml
  3. additionwas added to the residue, and insoluble materials
  4. filtrationwere filtered
  5. additionChloroform 50 ml was added to the organic layer
  6. customthe resulting precipitates
  7. customwere collected

Sources & evidence

ORD record
ord-d846d0a1c7c44e54b7b9fb5c6f5cbeca
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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