Acetic Acid → N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline

HRID 2258617

Reaction equation

HRID 2258617 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])(=[O:14])=[O:13])=[CH:8][CH:7]=1.C(O)(=O)C.N([O-])=O.[Na+]>O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:21]=[C:20]([F:22])[C:19]([N+:1]([O-:4])=[O:2])=[CH:18][C:17]=2[F:23])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 8500594N-(2,5-difluorophenyl)-4-methylbenzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 22921537N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroanilineYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A stirred solution of 20 mL (0.427 mole) of 90% nitric acid (fuming) in 170 mL of water was cooled in an ice-water bath, and 22.0 grams (0.077 mole) of N-(4-methylphenylsulfonyl)-2,5-difluoroaniline was added. To this mixture was added 170 mL of acetic acid and then 0.5 gram (0.008 mole) of sodium nitrite. Upon completion of the addition, the reaction mixture was warmed to 90° C., where it stirred for about 2.5 hours. The reaction mixture was then cooled and poured into cold water. The resultant precipitate was collected by filtration and dried, yielding about 25 grams of N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. temperatureThe reaction mixture was then cooled
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-53879eab8ecb4ad29f6f0088f467a3ce
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Linked notes

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