Sulfuric Acid → 6-(5-Isoquinolylsulfonyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one

HRID 619740Notes

Reaction equation

HRID 619740 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:15]4[NH:16][C:17](=[O:19])[O:18][C:14]=4[CH:13]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-:25].[Na+].S(=O)(=O)(O)[OH:28]>>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([C:12]3[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:15]4[NH:16][C:17](=[O:19])[O:18][C:14]=4[CH:13]=3)(=[O:28])=[O:25])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 218469496-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one

Product 1

HCID 218469446-(5-Isoquinolylsulfonyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-oneYield 39.1%

Procedure

6-(5-Isoquinolylsulfanyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazole-2-one 250 mg (0.7 mmol) was dissolved in concentrated sulfuric acid 2.5 ml, Beckmann's reagent 5.0 ml (K2Cr2O7 1 g, H2SO4 1 ml, H2O 9 ml) was added dropwise, and the mixture was stirred for 6 hours at room temperature. The reaction solution was neutralized with 4N sodium hydroxide, and the resulting precipitates were collected and washed with water, and 6-(5-isoquinolylsulfonyl)-5-nitro-2,3-dihydro-benzo[d][1,3]oxazol-2-one 110 mg (39.1%) was obtained.

Workup

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water

Sources & evidence

ORD record
ord-7b7d5caacbe24a8fb6797d56eb681523
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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