Urea → HCID 11075766, compound

HRID 2305977Notes

Reaction equation

HRID 2305977 reaction equation
[C:1]([C:3]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:4]=1[NH2:5])#[N:2].N(OS(=O)(=O)O)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:26]C(N)=O.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[N:5][C:4]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:3]=2[C:1]#[N:2])=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 1176UreaHCID 6115AnilineHCID 10340Sodium CarbonateHCID 82157Nitrosylsulfuric acidHCID 881692,4-Dicyanoaniline

Product 1

HCID 11075766HCID 11075766, compoundYield 183.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

31.4 g 2,4-dicyanoaniline were diazotised with 72 g nitrosylsulphuric acid at 0 to 5° C. in 300 ml of 50% aqueous sulphuric acid and the batch was subsequently stirred for 1 hour. The reaction mixture was slowly added to a solution of 20.4 g aniline and 4.5 g urea in 300 ml 50% aqueous sulphuric acid, the temperature being held at 0° C. After stirring for a further 1 hour, the pH of the reaction mixture was adjusted to 5.5 with sodium carbonate, and the precipitate was filtered off under suction, washed with water, and dried. 34 g of red 4-amino-2′,4′-dicyano-azobenzene were obtained. The product was used further without purification.

Workup

  1. custombeing held at 0° C
  2. stirringAfter stirring for a further 1 hour
  3. filtrationthe precipitate was filtered off under suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-efa8725ab0284276b339f81ae581167d
Source dataset
uspto-grants-2002_08
Patent number
US06441113B1

Reaction notes

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