Hydrochloric Acid → HCID 137226519, compound

HRID 2400178Notes

Reaction equation

HRID 2400178 reaction equation
Cl.N[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[NH3+][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N([O-])=[O:18].[Na+].[Cl-].[C:22]1([N+:28]#[N:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:30]1([CH:37]=[CH:36][CH:35]=[C:33]([OH:34])[CH:32]=1)[OH:31].[OH-:38].[Na+]>O.CO>[C:3]1([C:24]2[CH:25]=[C:26]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:27]([OH:38])=[C:22]([N:28]=[N:29][C:32]3[C:33]([OH:34])=[CH:35][CH:36]=[CH:37][C:30]=3[OH:31])[C:23]=2[OH:18])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 5054Resorcinol2×HCID 6115AnilineHCID 14798Sodium HydroxideHCID 60992Benzenediazonium chlorideHCID 21987731HCID 21987731, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 137226519HCID 137226519, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

Concentrated aqueous HCl (5 mL) is added to a slurry of aniline (1.88 g, 0.02 mol) in water (15 mL). The resultant anilinium hydrochloride is cooled to 0° C. and an aqueous solution of sodium nitrite (1.38 g, 0.02 mol in 5 mL water) is added thereto. The resultant phenyldiazonium chloride is combined with resorcinol (1.1 g, 0.01 mol), diluted to approximately 40 mL total volume with methanol, and slowly added to a -25° C. solution of sodium hydroxide (3 g) in methanol (120 mL). The total volume of the reaction medium is 160 mL, which also contains 12% water, a 2% load of theoretical product, and a 0.7% load of resorcinol. When the addition is complete, the methanol is removed by rotary evaporation, about 100 mL of water is added, and the remaining aqueous slurry is filtered through a celite plug. Concentrated HCl is added to the filtrate (to below pH 3) and the precipitate is filtered to give crude 4,6-bisphenylazoresorcinol (3 g) as a red solid. The material is recrystallized from chloroform/ethanol (40 mL/10 mL) to give pure 4,6-bisphenylazoresorcinol as red needles (2.35 g, 73%).

Workup

  1. additionWhen the addition
  2. customthe methanol is removed by rotary evaporation, about 100 mL of water
  3. additionis added
  4. filtrationthe remaining aqueous slurry is filtered through a celite plug
  5. additionConcentrated HCl is added to the filtrate (to below pH 3)
  6. filtrationthe precipitate is filtered
  7. customto give crude 4,6-bisphenylazoresorcinol (3 g) as a red solid
  8. customThe material is recrystallized from chloroform/ethanol (40 mL/10 mL)

Sources & evidence

ORD record
ord-34c86fa7d72f4d67903991315da118d7
Source dataset
uspto-grants-1995_09
Patent number
US05453542

Reaction notes

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