Nitric Acid → HCID 67405888, compound

HRID 1756777Notes

Reaction equation

HRID 1756777 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])([CH3:3])[CH3:2].[N+:24]([O-])([OH:26])=[O:25].N([O-])=O.[Na+]>O.C(O)(=O)C>[CH:1]([C:4]1[CH:9]=[C:8]([N+:24]([O-:26])=[O:25])[CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:15])=[O:16])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 836278N-[2,6-Di(propan-2-yl)phenyl]-4-methylbenzene-1-sulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 67405888HCID 67405888, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To 8.7 g of N-(2, 6-diisopropylphenyl)-p-toluenesulfonamide (8.7 g) were added 6.3 ml of 60% nitric acid, 50 ml of water and 50 ml of acetic acid, then 0.18 g of sodium nitrite, and the resultant mixture was stirred under refluxing and heating for 5 hours. After cooling, the reaction mixture was mixed with 200 ml of water, and the precipitated crystals were filtered and recrystallized from 50 ml of ethanol to give 4.7 g of N-(2, 6-diisopropyl-4-nitropheyl)-p-toluenesulfonamide. This compound was hydrolyzed in aqueous sulfuric acid to give 2.7 g of 2, 6-diisopropyl-4-nitroaniline.

Workup

  1. temperatureunder refluxing
  2. temperatureheating for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered
  5. customrecrystallized from 50 ml of ethanol

Sources & evidence

ORD record
ord-2a2aadb6b12b4be3a6acb19ce56b32db
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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