Water → N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

HRID 622191Notes

Reaction equation

HRID 622191 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[CH3:2].C(N(CC)CC)C.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.O>C(Cl)Cl>[CH2:20]([O:19][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[S:35]([C:32]1[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=1)(=[O:37])=[O:36])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 13911324HCID 13911324, compound

Product 1

HCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetalYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

59.46 g (0.2 mol) of N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (1) and 28.45 ml (0.204 mol) of triethylamine were dissolved in 100 ml of methylene chloride, to which 38.8 g (0.204 mol) of p-toluenesulfonyl chloride in 80 ml of methylene chloride was added dropwise at 15°-30° C. for 25 minutes. After stirring at room temperature for 30 minutes, 150 ml of water was added to the reaction mixture, which was stirred followed by liquid separation and then being washed with 100 ml of water. After drying the methylene chloride layer over anhydrous magnesium sulfate, the solvent was distilled off under vacuum to obtain 90.3 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (2) as an oil. Yield 100%. IR and NMR spectra of the resultant product are listed below. ##STR26##

Workup

  1. additionwas added dropwise at 15°-30° C. for 25 minutes
  2. stirringwas stirred
  3. customfollowed by liquid separation
  4. washbeing washed with 100 ml of water
  5. dry with materialAfter drying the methylene chloride layer over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-ee8a19f5cf454e9fa0d76b353b85bded
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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