Nitric Acid → HCID 18509253, compound

HRID 1356656Notes

Reaction equation

HRID 1356656 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])#[N:2].[N+:20]([O-])([OH:22])=[O:21]>C(OC(=O)C)(=O)C>[C:1]([C:3]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:4]=1[NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 561404HCID 561404, compound

Product 1

HCID 18509253HCID 18509253, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a suspension of 2′-cyano-p-toluenesulfonanilide (2.67g (9.80 mmol) in acetic anhydride (7.0 ml), 97% fuming nitric acid (0.45 ml (10.5 mmol) was added with stirring at room temperature. After stirring for one hour at 50° C., crystals began to separate. Water was added to decompose excess acetic anhydride, and the crystals were filtered, washed with water, dried in the air and then, washed with diethyl ether and collected by filtration to give 3.05 g (98%) of 2′-cyano-4′-nitro-p-toluenesulfonanilide as pale yellow crystals.

Workup

  1. stirringAfter stirring for one hour at 50° C.
  2. customto separate
  3. additionWater was added
  4. filtrationthe crystals were filtered
  5. washwashed with water
  6. customdried in the air
  7. washwashed with diethyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-94f29435512546109a4ade90fe6c3756
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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