Hydrochloric Acid → Benzoyl chloride

HRID 483597Notes

Reaction equation

HRID 483597 reaction equation
NC1C=CC(NC2C=C3C(=CC=2)C(O)=CC(S(O)(=O)=O)=C3)=CC=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([Cl:31])=[O:30])=[CH:27][CH:26]=1.[OH-].[Na+].[ClH:36].[Cl-].[Na+]>O>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([Cl:31])=[O:30])=[CH:27][CH:26]=1.[C:29]([Cl:31])(=[O:30])[C:28]1[CH:32]=[CH:33][CH:25]=[CH:26][CH:27]=1.[Cl:36][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:25]=1)[C:29]([Cl:31])=[O:30]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 1171547-(4-Aminoanilino)-4-hydroxynaphthalene-2-sulfonic acid

Product 3

HCID 7412Benzoyl chlorideHCID 85014-Chlorobenzoyl chlorideHCID 69252Benzoyl chloride, 3-chloro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.5 parts of 6-(4'-aminophenylamino)-1-hydroxynaphthalene-3-sulfonic acid are dissolved in 1500 parts of hot water. After cooling down to room temperature, 9.65 parts of 4-chlorobenzoyl chloride are added dropwise in the course of about 30 minutes and the reaction mixture is reacted at a pH maintained at 6 until the consumption of sodium hydroxide solution has ceased (duration about 2.5 to 4 hours). Then the pH is adjusted to 1 with hydrochloric acid and the product is salted out with sodium chloride. Filtering off with suction and drying gives the compound of the formula ##STR72## The replacement of 4-chlorobenzoyl chloride with an equivalent amount of benzoyl chloride or 3-chlorobenzoyl chloride gives analogous intermediates.

Workup

  1. customthe reaction mixture is reacted at a pH
  2. filtrationFiltering off with suction
  3. customdrying

Sources & evidence

ORD record
ord-b0a1af2c6420433f8e798ea5ba82c7f8
Source dataset
uspto-grants-1993_07
Patent number
US05225545

Reaction notes

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