Hydrochloric Acid → HCID 14876106, compound

HRID 1197214Notes

Reaction equation

HRID 1197214 reaction equation
[CH:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[S:11]([OH:14])(=[O:13])=[O:12])[NH2:7])=O.[C:15](OC(=O)C)(=O)C.S(OCC)(OCC)(=O)=O.[OH-].[Na+].Cl.[Cl-].[Na+]>O>[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[S:11]([OH:14])(=[O:13])=[O:12])[NH2:7])[CH3:15]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6163Diethyl SulfateHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 14876104HCID 14876104, compound

Product 1

HCID 14876106HCID 14876106, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

220 g of 3-(N-formylamino)aniline-4-sulfonic acid in 1,500 ml of water were reacted with 140 g of acetic anhydride at a pH of 5.0 to 5.5. The mixture was heated, at pH 7.0, to 50° C., and 200 g of diethyl sulfate were added. The pH was then adjusted to 12.5 to 13.0 with caustic soda solution and stirring was continued for 2 hours. The pH was then adjusted to -0.5 to 0 with hydrochloric acid, and the mixture was boiled under reflux at 100° C. for 3 hours. After cooling, it was adjusted to pH 1.0 with caustic soda solution, and 200 g of sodium chloride were added. The precipitated 3-(N-ethylamino)aniline-4-sulfonic acid was then isolated by filtration in vacuo.

Workup

  1. temperatureunder reflux at 100° C. for 3 hours
  2. temperatureAfter cooling
  3. additionwere added

Sources & evidence

ORD record
ord-b9b0a02ee2b14ccf9fc9b50240ac1acb
Source dataset
uspto-grants-1992_05
Patent number
US05117050

Reaction notes

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