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

HRID 1088923Notes

Reaction equation

HRID 1088923 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:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>C(N(CC)CC)C.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:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29])[CH3:21]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (2) in an amount of 59.46 g (0.2 mol) and triethylamine in an amount of 28.45 ml (0.204 mol) were dissolved in 100 ml of methylene chloride, to which 38.88 g (0.204 mol) of p-toluenesulfonyl chloride in 80 ml of methylene chloride was added dropwise at 15°-30° C. over 25 minutes After stirring the mixture at room temperature for 30 minutes, 150 ml of water was added and the reaction mixture was stirred. The methylene chloride layer was separated from the aqueous layer and further washed with 100 ml of water. After drying the methylene chloride layer over anhydrous magnesium sulfate, the solvent was distilled off at reduced pressure to obtain 90.3 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (3) as an oil. Yield: 100%. IR and NMR of the resultant product are listed below.

Workup

  1. additionwas added dropwise at 15°-30° C. over 25 minutes
  2. stirringthe reaction mixture was stirred
  3. customThe methylene chloride layer was separated from the aqueous layer
  4. washfurther 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 at reduced pressure

Sources & evidence

ORD record
ord-65387d2b0b094411a9607cccc19464fa
Source dataset
uspto-grants-1990_10
Patent number
US04963684

Reaction notes

Loading…