Acetic Acid → MLS002703379

HRID 484784Notes

Reaction equation

HRID 484784 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+:20]([O-])([OH:22])=[O:21].C(O)(=O)C.N([O-])=O.[Na+]>O>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:12]=2[CH3:18])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 262999N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 263000MLS002703379

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The sulfonamide intermediate of Example 4 (6.9 g, 0.025 mole) was added to a solution of 6.3 ml of concentrated nitric acid in 50 ml of water, followed by addition of 50 ml of glacial acetic acid and 0.18 g of sodium nitrite. The mixture was heated at reflux for one hour, then poured into 100 ml of water. The crude product thus isolated was recrystallized from ethanol to give 6.5 g of the title compound. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. customThe crude product thus isolated
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-608ef35de8e148e19da0a0f8ad804523
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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