Hydrochloric Acid → HCID 136333708, compound

HRID 1955370Notes

Reaction equation

HRID 1955370 reaction equation
[N:1]([O-])=O.[Na+].Cl.[S:6]([OH:16])(=[O:15])([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=O.[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[OH:25].[OH-].[Na+]>O>[Cl:24][C:23]1[C:18]([Cl:17])=[C:19]([OH:25])[CH:20]=[CH:21][C:22]=1[N:1]=[N:14][C:11]1[CH:10]=[CH:9][C:8](=[S:6](=[O:15])=[O:16])[CH2:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 8479Sulfanilic acidHCID 113342,3-DichlorophenolHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 136333708HCID 136333708, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

At 0 to 5° C., a solution of 7.6 g (0.11 mol) of NaNO2 in 12 ml of H2O is added dropwise to 50 ml of aqueous HCl (15%) and 18.1 g (0.105 mol) of sulphanilic acid in a 100 ml two-neck flask fitted with internal thermometer and magnetic stirrer. After 1 hour, this diazonium salt suspension is added at 5 to 10° C. to a solution of 16.3 g (0.1 mol) of 2,3-dichlorophenol and 20 g (0.5 mol) of NaOH in 200 ml of H2O. The mixture is allowed to warm to room temperature, stirred for a further 4 hours and neutralized with aqueous HCl, and the precipitated solid is filtered off with suction using a suction filter. Recrystallization from 200 ml of toluene and 20 ml of methanol affords 26.3 g (83.5% of theory) of pure (2,3-dichloro-4-hydroxyphenyl)-4-sulphonylphenyldiazene.

Workup

  1. customfitted with internal thermometer and magnetic stirrer
  2. filtrationthe precipitated solid is filtered off with suction
  3. filtrationfilter
  4. customRecrystallization from 200 ml of toluene and 20 ml of methanol

Sources & evidence

ORD record
ord-c34bb63300a7416599dbf18c7f34eab3
Source dataset
uspto-grants-2000_09
Patent number
US06124504

Reaction notes

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