Hydrochloric Acid → HCID 20184573, compound

HRID 2309912Notes

Reaction equation

HRID 2309912 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH3:10][O:11][C:12]1[CH:20]=[C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:17][C:13]=1[C:14](O)=O.Cl>P(Cl)(Cl)(Cl)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:14]([C:13]3[CH:17]=[CH:18][C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][C:12]=3[O:11][CH3:10])[NH:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27729703,4-DiaminophenolHCID 121193062-Methoxy-4-[(methylsulfonyl)amino]benzoic acid

Product 1

HCID 20184573HCID 20184573, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Quantities of 1.6 gm (10 mmol) of 4-hydroxy-1,2-phenylenediamine and 4.9 gm (20 mmol) of 2-methoxy-4-methansulfonylamino-benzoic acid were refluxed for 1.5 hours, under stirring, in 80 ml of phosphorus oxychloride. The resulting dark solution was then decanted off to eliminate any undissolved components, the phosphorus oxychloride was distilled off in vacuo, and the residue was carefully mixed with 10 gm of crushed ice. Ten milliliters of 4N sodium hydroxide were added to the suspension thus obtained, and the resulting mixture was stirred for one hour at ambient temperature. It was then neutralized with concentrated hydrochloride acid, while being cooled, the solution was evaporated in vacuo to about 3 to 4 ml, the crude product precipitate was subjected to suction filtration, and the resultant crude product was purified by chromatography (250 gm of silica gel, eluant: methylene chloride with 5% ethanol).

Workup

  1. customThe resulting dark solution was then decanted off
  2. distillationthe phosphorus oxychloride was distilled off in vacuo
  3. additionthe residue was carefully mixed with 10 gm of crushed ice
  4. additionTen milliliters of 4N sodium hydroxide were added to the suspension
  5. customthus obtained
  6. temperaturewhile being cooled
  7. customthe solution was evaporated in vacuo to about 3 to 4 ml
  8. filtrationthe crude product precipitate was subjected to suction filtration
  9. customthe resultant crude product was purified by chromatography (250 gm of silica gel, eluant: methylene chloride with 5% ethanol)

Sources & evidence

ORD record
ord-3eadae1f408a455b84fa2c42f1706fd3
Source dataset
uspto-grants-1987_09
Patent number
US04696931

Reaction notes

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