Acetic Acid → N-Benzyl-N-nitroso-p-toluenesulfonamide

HRID 1941464

Reaction equation

HRID 1941464 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[N:23]([O-])=[O:24].[Na+]>C(OC(=O)C)(=O)C>[N:23]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 95801p-Toluenesulfonamide, N-benzyl-HCID 23668193Sodium Nitrite

Product 1

HCID 4118076N-Benzyl-N-nitroso-p-toluenesulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of N-benzyl-p-toluenesulphonamide (21 g, 80 mmol) and acetic acid (100 ml) in acetic anhydride (400 ml) was added solid sodium nitrite (120 g, 1.7 mol) in portions over a period of 12 hours at 5° C. The temperature was kept below 10° C. all the time. After the addition was finished the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was poured over an excess of ice water and stirred for 1 hour. The pale yellow precipitate was filtered and washed several times with water. The crude product was recrystallized from ethanol to give the title compound as a tiny yellow needles (19.1 g, 82% yield, m.p. 92°-93° C., (Lit.1 89°-90° C.). δH (CDCl3): 7.80(2H,m); 7.25(7H,m); 4.95(2H,s); 2.40(3H,s)ppm.

Workup

  1. customwas kept below 10° C.
  2. additionAfter the addition
  3. stirringstirred for 1 hour
  4. filtrationThe pale yellow precipitate was filtered
  5. washwashed several times with water
  6. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-244b407151ac4928a3fd3827f72bd3a6
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Linked notes

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