Sodium Hydroxide → HCID 19887564, compound

HRID 654463Notes

Reaction equation

HRID 654463 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:6]=1[N:13](S(C1C=CC(Cl)=CC=1)(=O)=O)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])C.[OH-].[Na+]>C(O)C>[Cl:12][C:7]1[C:6]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:15])=[O:16])=[C:5]([CH:10]=[C:9]([Cl:11])[CH:8]=1)[C:4]([OH:34])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54274117HCID 54274117, compound

Product 1

HCID 19887564HCID 19887564, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 27.0 g of 3,5-dichloro-2-[di-(4-chlorophenylsulfonyl)-amino]-benzoic acid ethyl ester, 139 ml of 2N sodium hydroxide solution and 140 ml of ethanol is boiled at reflux for 6 hours, the solid gradually dissolving. After the reaction mixture has cooled, the precipitated crystals are filtered off and dissolved in 400 ml of water. 400 ml of methanol are added, acidification with 2N hydrochloric acid is carried out, and the precipitated crystals are filtered off. 12.3 g of the title compound (m.p. 188°-190° C.) are obtained.

Workup

  1. temperatureat reflux for 6 hours
  2. dissolutionthe solid gradually dissolving
  3. temperatureAfter the reaction mixture has cooled
  4. filtrationthe precipitated crystals are filtered off
  5. dissolutiondissolved in 400 ml of water
  6. addition400 ml of methanol are added
  7. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-f787877e7e4444079246f8e99c2721fc
Source dataset
uspto-grants-1992_07
Patent number
US05132314

Reaction notes

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