4-Toluenesulfonyl chloride → HCID 19773482, compound

HRID 1614283Notes

Reaction equation

HRID 1614283 reaction equation
O[CH2:2][CH2:3][N:4]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)[CH3:5].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[S:20]([CH2:2][CH2:3][N:4]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)[CH3:5])([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 36143164-[(2-Hydroxyethyl)(methyl)amino]benzaldehyde

Product 1

HCID 19773482HCID 19773482, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.5 mol of 4-[N-2-hydroxyethyl-N-methylamino]benzaldehyde in methylene chloride at 0° C. are added 0.51 mol of p-toluenesulfonyl chloride, 0.51 mol of triethylamine, and 0.005 mol of N,N-dimethylaminopyridine, and the reaction medium is warmed slowly to room temperature. After standing at room temperature for one hour, the reaction product medium is washed with cold 1N HCL, saturated sodium bicarbonate solution, and water. The organic solution is separated and dried over molecular sieves, filtered through cotton, and evaporated to yield the 4-[N-2-tosylethyl-N-methylamino]-benzaldehyde as a crystalline product, which then is recrystallized from ethanol.

Workup

  1. customthe reaction
  2. washthe reaction product medium is washed with cold 1N HCL, saturated sodium bicarbonate solution, and water
  3. customThe organic solution is separated
  4. customdried over molecular sieves
  5. filtrationfiltered through cotton
  6. customevaporated

Sources & evidence

ORD record
ord-1ffd4e61dc8c4ecdb51f4c859188c7de
Source dataset
uspto-grants-1993_03
Patent number
US05196509

Reaction notes

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