Nitric Acid → HCID 18509257, compound

HRID 1356662Notes

Reaction equation

HRID 1356662 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].O>C(O)(=O)C>[F:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([N+:19]([O-:21])=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 853960p-Toluenesulfonanilide, 4'-fluoro-

Product 1

HCID 18509257HCID 18509257, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4′-fluoro-p-toluenesulfonanilide (486.6 g (1.80 mol) in acetic acid (955 ml), 97% fuming nitric acid (128.6 g (1.98 mol) was added dropwise, keeping the inner temperature at 45° C., over a period of 40 minutes. After completion of the addition, the reaction mixture was stirred at 50° C. for 2 hours and left to cool to room temperature. Water (2000 ml) was then added and the mixture was stirred for 30 minutes. The crystals separated were filtered and washed with water to give 543.5 g (97%) of 4′-fluoro-2′-nitro-p-toluenesulfonanilide as yellow crystals.

Workup

  1. customat 45° C.
  2. additionAfter completion of the addition
  3. waitleft
  4. temperatureto cool to room temperature
  5. stirringthe mixture was stirred for 30 minutes
  6. customThe crystals separated
  7. filtrationwere filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-13e55f2a2391422388b940b3966c10d5
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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