Hydrochloric Acid → HCID 23670666, compound

HRID 2293619Notes

Reaction equation

HRID 2293619 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:17]([OH:20])(=[O:19])=[O:18].Cl.N([O-])=O.[Na+:25].[PH2](O)=O>O>[Na+:25].[CH3:16][C:8]([C:5]1[CH:4]=[C:3]([S:17]([O-:20])(=[O:19])=[O:18])[CH:2]=[CH:7][CH:6]=1)([CH3:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 4124402Phosphinic AcidHCID 10803520HCID 10803520, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23670666HCID 23670666, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

1-Amino-4-(α,α-dimethylbenzyl)benzene-2-sulphonic acid (582.7 g) is suspended in water (41) in a 201 reaction vessel, cone. HCl is added (400 ml) and the mixture is stirred and heated at 65° C. for 20 minutes. The suspension is cooled to 20° C. and cone. HCl (400 ml) is added, followed by a solution of NaNO2 (138 g) in water (400 ml) dropwise, maintaining the temperature below 25° C. The resulting mixture is stirred at room temperature for a further 30 minutes. 50% Hypophosphorous acid (1.7 kg) is added dropwise over 30 minutes and the mixture is stirred at room temperature for 1 hour. The mixture is then warmed slowly until a temperature of 60° C. is reached and foaming has subsided to give a dark brown solution which is allowed to cool overnight and then filtered to remove a small amount of solid. The filtrate is evaporated to a volume of 41, neutralised by the gradual addition of sodium hydroxide pellets (950 g) to pH 10-11, water (31) is added and the solution warmed to 70° C. NaCl (800 g) is added and the product is allowed to crystallise. The solid is collected by filtration, washed with saturated brine and dried. After recrystallisation from 15% w/v NaCl(aq), the solid is stirred with ice water to remove salt, filtered and dried, stirred in acetone, filtered off and dried to give 3-(α,α-dimethylbenzyl)benzenesulphonic acid sodium salt. Further product is recovered from the washings.

Workup

  1. temperatureThe suspension is cooled to 20° C.
  2. temperaturemaintaining the temperature below 25° C
  3. stirringThe resulting mixture is stirred at room temperature for a further 30 minutes
  4. stirringthe mixture is stirred at room temperature for 1 hour
  5. temperatureThe mixture is then warmed slowly until a temperature of 60° C.
  6. customto give a dark brown solution which
  7. temperatureto cool overnight
  8. filtrationfiltered
  9. customto remove a small amount of solid
  10. customThe filtrate is evaporated to a volume of 41
  11. additionneutralised by the gradual addition of sodium hydroxide pellets (950 g) to pH 10-11, water (31)
  12. additionis added
  13. temperaturethe solution warmed to 70° C
  14. additionNaCl (800 g) is added
  15. customto crystallise
  16. filtrationThe solid is collected by filtration
  17. washwashed with saturated brine
  18. customdried
  19. customAfter recrystallisation from 15% w/v NaCl(aq)
  20. stirringthe solid is stirred with ice water
  21. customto remove salt
  22. filtrationfiltered
  23. customdried
  24. stirringstirred in acetone
  25. filtrationfiltered off
  26. customdried

Sources & evidence

ORD record
ord-72730d41fca44f58ad721a97b15c3bd8
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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