Sulfuric Acid → HCID 178509788, compound

HRID 1283797Notes

Reaction equation

HRID 1283797 reaction equation
S(=O)(=O)(O)O.[C:6]([C:8]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:9]=1[NH2:10])#[N:7].[N:19]([O-])=O.[Na+].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C.O>[C:6]([C:8]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][C:9]=1[NH:10][N:19]=[N:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:7]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6115Aniline2×HCID 134390282-Amino-4-(trifluoromethyl)benzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178509788HCID 178509788, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A cooled solution of 3.6 ml. of concentrated sulfuric acid and 3.6 ml. of water is added to 3.0 g. (0.016 mol.) of 2-cyano-5-trifluoromethylaniline. The slurry is cooled (ice bath) and stirred and a solution of 1.1 g. (0.016 mol.) of sodium nitrite in 6 ml. of water is added dropwise. The resulting mixture is then added to a solution of 3 ml. of aniline in 120 ml. of ethanol. Additional aniline (6 ml.) is added and the reaction mixture is stirred for 15 minutes. The mixture is poured into 500 ml. of water and the precipitate is collected by filtration, washed with water and recrystallized from hexane to give 3-(2-cyano-5-trifluoromethylphenyl)-1-phenyltriazene, m.p. 139°-141°.

Workup

  1. temperatureThe slurry is cooled (ice bath)
  2. additionThe resulting mixture is then added to a solution of 3 ml
  3. stirringthe reaction mixture is stirred for 15 minutes
  4. additionThe mixture is poured into 500 ml
  5. filtrationof water and the precipitate is collected by filtration
  6. washwashed with water
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-77be530c58eb4d2d9935e043fc4d4b2d
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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