Hydrochloric Acid → 2,6-Diethylphenyl-p-toluenesulfonamide

HRID 329601Notes

Reaction equation

HRID 329601 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1N)[CH3:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl.[N:24]1C=CC=CC=1>>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[C:13]1[CH:14]=[C:15]([S:18]([NH2:24])(=[O:20])=[O:19])[CH:16]=[CH:17][C:12]=1[CH3:22])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 113692,6-Diethylaniline

Product 1

HCID 678930812,6-Diethylphenyl-p-toluenesulfonamide

Procedure

To 29.85 g (0.200 mol) of 2,6-diethylaniline in 100 ml of pyridine was added 41.94 g (0.220 mol) of p-toluenesulfonyl chloride in portions at 10° to 4° C. The reaction mixture was stirred overnight, poured into 1 l of 10% hydrochloric acid, filtered, washed three times with water, dissolved in CHCl3, dried over MgSO4, and evaporated to dryness to yield 61.48 g (101.3%) of crude product. A portion (46.3 g) was recrystallized from cyclohexane to yield 33.1 g of 2,6-diethylphenyl-p-toluenesulfonamide, mp. 133.4°. NMR (CDCl3): δ 1.05 (t, 6H), 2.45 (m, 7H), 6.10 (s, 1H), 6.9-7.3 (m, 5H), 7.5-7.7 (d, 2H).

Workup

  1. filtrationfiltered
  2. washwashed three times with water
  3. dissolutiondissolved in CHCl3
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customto yield 61.48 g (101.3%) of crude product
  7. customA portion (46.3 g) was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-1ae72f8d136e4134ae84dde9c31c1104
Source dataset
uspto-grants-1990_01
Patent number
US04892871

Reaction notes

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