Acetic Acid → Benzenesulfonamide, N-(2,6-diethyl-4-nitrophenyl)-4-methyl-

HRID 26023

Reaction equation

HRID 26023 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[C:8]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH3:6].C(O)(=O)C.N([O-])=O.[Na+]>O>[CH2:5]([C:7]1[CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=[C:9]([CH2:13][CH3:14])[C:8]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:17])=[O:18])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 7315352',6'-Diethyl-p-toluenesulfonanilideHCID 23668193Sodium Nitrite

Product 1

HCID 155515Benzenesulfonamide, N-(2,6-diethyl-4-nitrophenyl)-4-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 115 ml nitric acid (d=1.42) in water (900 ml) are added successively 129.9 g (0.43 moles) of N-(2,6-diethylphenyl)-p-toluenesulfonamide, glacial acetic acid (900 ml) and sodium nitrite (3.2 g). The mixture is boiled on a steam bath for 1.5 hours, then poured into ice water (2 l). The precipitate is filtered, washed with water and air-dried to give crude N-(2,6-diethyl-4-nitrophenyl)-p-toluenesulfonamide.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-317d65b476f84153aac3960827a0265d
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Linked notes

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