Hydrochloric Acid → HCID 13668876, compound

HRID 247156Notes

Reaction equation

HRID 247156 reaction equation
[Na].Cl[C:3]1([N+]([O-])=O)[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH2:4]1.[SH2:16].[Na].[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1)([O-])=O.[OH-].[Na+].Cl.O.[NH3:34]>O>[NH2:18][C:21]1[CH:29]=[CH:28][C:24]([C:25]2[S:16][C:3]3[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][C:4]=3[N:34]=2)=[CH:23][CH:22]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 12896473Azane;hydrateHCID 86586439Sodium hydrogen sulphide2×HCID 86741867HCID 86741867, compound

Product 1

HCID 13668876HCID 13668876, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

158 g of the sodium salt of 4-chloro-4-nitro benzenesulphonic acid (technical, about 83% pure) are dissolved at about 80° C. in 400 ml of water. 180 ml of 30% strength aqueous sodium hydrogen sulphide solution (technical) are added dropwise in the course of about 30 minutes. The mixture is then stirred at 90° C. for one hour and is then cooled down to 70° C., and at at this temperature 93 g of 4-nitrobenzoyl chloride are added. The pH of the mixture is held at 8 by addition of sodium hydroxide solution. As soon as the pH remains constant, 180 ml of 30% strength aqueous sodium hydrogen sulphide solution are added, and the reaction mixture is boiled under reflux for one hour. The reaction mixture is then brought to pH 1 with hydrochloric acid and is boiled under reflux for 5 hours. After cooling down, the precipitated product is isolated. The crude product is heated to 90° C. in a mixture of 300 ml of water and 150 ml of 20% strength ammonia water. The mixture is filtered while still hot, and 50 g of sodium chloride are added to the filtrate while still hot. On cooling down, 125 g of pure product of the formula ##STR20## crystallise out.

Workup

  1. temperatureis then cooled down to 70° C.
  2. temperatureunder reflux for one hour
  3. temperatureunder reflux for 5 hours
  4. temperatureAfter cooling down
  5. customthe precipitated product is isolated
  6. filtrationThe mixture is filtered while still hot, and 50 g of sodium chloride
  7. additionare added to the filtrate while still hot
  8. temperatureOn cooling down
  9. custom125 g of pure product of the formula ##STR20## crystallise out

Sources & evidence

ORD record
ord-b712528fa2df4243886bfe274dd1b960
Source dataset
uspto-grants-1987_11
Patent number
US04705861

Reaction notes

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