Phenol → HCID 136117602, compound

HRID 1350353Notes

Reaction equation

HRID 1350353 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.P(=O)(O)(O)O.S(=O)(=O)(O)O.[C:29]1([OH:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH2:36]C(N)=O.[OH-].[Na+]>O.C(O)(=O)C>[OH:35][C:29]1[CH:34]=[CH:33][C:32]([N:36]=[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:31][CH:30]=1

Participants

10

Reactant 7

HCID 996PhenolHCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 1176UreaHCID 14798Sodium HydroxideHCID 82157Nitrosylsulfuric acidHCID 881692,4-Dicyanoaniline

Product 1

HCID 136117602HCID 136117602, compoundYield 244.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

20.7 g 2,4-dicyanoaniline were diazotised with 48 g nitrosylsulphuric acid at 0 to 5° C. in a solution comprising 200 ml glacial acetic acid, 40 ml of 85% phosphoric acid and 7.5 ml of concentrated aqueous sulphuric acid, and the batch was subsequently stirred for 1 hour. The reaction mixture was slowly added to a solution of 16 g phenol and 3 g urea in 120 ml water, the temperature being held at 10° C. and the pH being maintained at 6.3–6.5 with caustic soda solution. After stirring for a further 1 hour, the precipitate was filtered off under suction, washed with water, dried, and recrystallised from toluene. 30.3 g of orange-red 4-hydroxy-2′,4′-dicyano-azobenzene were obtained.

Workup

  1. custombeing held at 10° C.
  2. stirringAfter stirring for a further 1 hour
  3. filtrationthe precipitate was filtered off under suction
  4. washwashed with water
  5. customdried
  6. customrecrystallised from toluene

Sources & evidence

ORD record
ord-4e83b92d5bd640acb4d0dc7460982043
Source dataset
uspto-grants-2007_05
Patent number
US07214752B2

Reaction notes

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