Hydrochloric Acid → HCID 22483910, compound

HRID 1168127Notes

Reaction equation

HRID 1168127 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]1([S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.Cl>O>[C:9]1([S:15]([NH:18][C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[CH:3]=2)=[O:20])(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 115683-AminophenolHCID 14798Sodium Hydroxide2×HCID 76096Phenylsulphonyl isocyanate

Product 1

HCID 22483910HCID 22483910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5.65 g m-aminophenol in 45m-acetonitrile was added dropwise 9.5 g benzenesulphonylisocyanate such that the temperature was maintained at <40° C. The mixture was stirred for one hour at room temperature and allowed to stand overnight. To the reaction was then added 25ml water and 5.35 g 47% caustic soda and the reaction was heated to 55-60° C. To this was added, over two hours, 9.93 g p-toluenesulphonylchloride with simultaneous addition of 47% caustic soda so as to maintain the pH between 10 and 11. After two hours at 60° C. the reaction mass was neutralised with hydrochloric acid to produce a thick white precipitate of the desired product. This was isolated by filtration and washed with water to give after drying 21.1 g of product, melting point 162-170° C.

Workup

  1. temperaturewas maintained at <40° C
  2. waitto stand overnight
  3. temperaturethe reaction was heated to 55-60° C
  4. additionTo this was added, over two hours
  5. temperatureto maintain the pH between 10 and 11

Sources & evidence

ORD record
ord-b138f1df009547a2a44e782a9a944d8f
Source dataset
uspto-grants-2003_09
Patent number
US06624117B1

Reaction notes

Loading…