Sodium Hydroxide → N-(4-Formyl-3-hydroxyphenyl)benzenesulphonamide

HRID 1679314Notes

Reaction equation

HRID 1679314 reaction equation
O=C1N(C)C(=O)N(C)[CH:4]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:13][C:12]=2[OH:27])N1C.[OH-:29].[Na+]>O>[C:21]1([S:18]([NH:17][C:14]2[CH:13]=[C:12]([OH:27])[C:11](=[CH:16][CH:15]=2)[CH:4]=[O:29])(=[O:20])=[O:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70620340HCID 70620340, compound

Product 1

HCID 819586N-(4-Formyl-3-hydroxyphenyl)benzenesulphonamideYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

432 g (1 mol) of 2,4-dioxo-hexahydro-1,3,5-trimethyl-6-[2-hydroxy-4-benzenesulphonamido-phenyl]-s-triazine (93.5% pure product) are introduced into a solution of 280 g (7 mols) of sodium hydroxide in 600 ml of water. The mixture is boiled under reflux for 6 hours, under nitrogen. A pale brown solution is formed, from which individual small crystals separate out. The contents of the flask are then poured onto a mixture of 700 ml of concentrated hydrochloric acid and 2 kg of ice and the yellow product which has separated out is filtered off. After washing with water and drying at 80° C, 274 g of 4-benzenesulphonamidosalicylaldehyde with a melting point of 150° to 157° C are obtained. According to the oxime titration, the aldehyde is 94.8% pure and the yield is thus 93.6%. After redissolving in xylene (1 : 10), the aldehyde is obtained as colorless crystals with a melting point of 160° to 163° C.

Workup

  1. temperatureunder reflux for 6 hours, under nitrogen
  2. customA pale brown solution is formed, from which individual small crystals
  3. customseparate out
  4. additionThe contents of the flask are then poured onto a mixture of 700 ml of concentrated hydrochloric acid and 2 kg of ice
  5. customthe yellow product which has separated out
  6. filtrationis filtered off
  7. washAfter washing with water
  8. customdrying at 80° C

Sources & evidence

ORD record
ord-4b4dd161d3c442399a55ea97ea6db843
Source dataset
uspto-grants-1978_03
Patent number
US04080379

Reaction notes

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