4-Toluenesulfonyl chloride → Benzenesulfonamide, N-(5-hydroxy-1-naphthalenyl)-4-methyl-

HRID 2287009Notes

Reaction equation

HRID 2287009 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[C:7]3[OH:12])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 657465-Amino-1-naphthol2×

Product 1

HCID 104703Benzenesulfonamide, N-(5-hydroxy-1-naphthalenyl)-4-methyl-Yield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1 mole 5-amino-1-naphthol in dry pyridine was stirred at 0° C. and treated portionwise with 1 mole of p-toluenesulfonyl chloride. When anaylsis showed that the 5-amino-1-naphthol was consumed the reaction mixture was poured onto a sufficient quantity of aqueous hydrogen chloride to neutralize the excess pyridine and allow separation of the product as a fine powder which was filtered, washed with water, and recrystallized from ethanol to obtain (96% yield) analytically pure 5-p-toluenesulfonamido-1-naphthol having a melting point of 182°-194° C. Next, 2.58 g. (4.00 mmol) of 4-(m-aminophenylsulfonamido)-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-1-hydroxy-2-naphthamide were dissolved in 10 ml. dry pyridine and treated with 50 ml. 5:1 acid and 10 ml. concentrated hydrochloric acid. The clear solution was cooled to 0° C. and treated with a solution of 284 mg. (4.00 mmol) sodium nitrite in 3 ml. of ice water. The resulting orange solution was added rapidly to a solution of 1.25 g. (4.00 mmol) of the above sulfonamidonaphthol dissolved in 8 ml. dry pyridine and 50 ml. 5:1 acid, and cooled to 5° C. The orange dye formed immediately. After 40 minutes at 5°-10°, the dye was precipitated by adding 300 ml. ice water and adjusting the pH to 2 with concentrated HCl. The orange powder obtained by filtration was washed with 8 liters of water and dried to give 3.31 g. Compound 12. This compound was tested in a manner similar to that of Example 12A and the released dye was found to have a λ max of 555 nm. The Dmax of transferred image was 0.97.

Workup

  1. customwas consumed the reaction mixture
  2. additionwas poured onto a sufficient quantity of aqueous hydrogen chloride
  3. customseparation of the product as a fine powder which
  4. filtrationwas filtered
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-268c87b8a13342779db56fd936892292
Source dataset
uspto-grants-1981_05
Patent number
US04268606

Reaction notes

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