Nitric Acid → 2'-Nitro-4'-thiocyano-p-toluenesulfonanilide

HRID 1356673

Reaction equation

HRID 1356673 reaction equation
[S:1]([C:4]1[CH:20]=[CH:19][C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)[C:2]#[N:3].[N+:21]([O-])([OH:23])=[O:22].O>C(O)(=O)C>[N+:21]([C:6]1[CH:5]=[C:4]([S:1][C:2]#[N:3])[CH:20]=[CH:19][C:7]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 8034834-{[(4-Methylphenyl)sulfonyl]amino}phenyl thiocyanate

Product 1

HCID 185092522'-Nitro-4'-thiocyano-p-toluenesulfonanilideYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4′-Thiocyano-p-toluenesulfonanilide (19.2 g (63.2 mmol)) was dissolved in acetic acid (60 ml). To this, fuming nitric acid (3.04 ml (75.9 mmol)) was added dropwise with stirring at room temperature. Then, the mixture was stirred at 50° C. for 4 hours, poured into water, and the crystals separated were filtered and washed with water. The resulting crystals were dissolved in ethyl acetate, and the solution was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 21.8 g (99%) of 2′-nitro-4′-thiocyano-p-toluenesulfonanilide as pale yellow crystals.

Workup

  1. stirringThen, the mixture was stirred at 50° C. for 4 hours
  2. customthe crystals separated
  3. filtrationwere filtered
  4. washwashed with water
  5. dissolutionThe resulting crystals were dissolved in ethyl acetate
  6. dry with materialthe solution was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10eeae91fe154df3aab70945d8b1ac0a
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Linked notes

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