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

HRID 622197Notes

Reaction equation

HRID 622197 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=[CH:22][C:9]=1[CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[CH2:29]([O:31][CH:32]([O:35][CH2:36][CH3:37])[CH2:33]Br)[CH3:30]>O>[CH2:29]([O:31][CH:32]([O:35][CH2:36][CH3:37])[CH2:33][N:11]([CH2:10][C:9]1[CH:22]=[CH:23][C:24]2[O:28][CH2:27][O:26][C:25]=2[C:8]=1[O:7][CH3:6])[S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH3:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 21294012N-(2-methoxy-3,4-methylenedioxybenzyl)-p-toluenesulfonamide

Product 1

HCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetalYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

44 mg (1.1 mmol) of 60% oil dispersion of sodium hydride was washed twice with 2 ml of dry hexane to eliminate oil. 2 ml of dry N,N-dimethylformamide, 335 mg (1 mmol) of N-(2-methoxy-3,4-methylenedioxybenzyl)-p-toluenesulfonamide (1) and 0.18 ml (1.1 mmol) of bromoacetaldehyde diethylacetal (purity 95%) were added in order. The resulting mixture was stirred at 100° C. for 10 hours. On cooling, to this 5 ml of water was added and the reaction mixture was extracted with 8 ml and then 2 ml of methylene chloride successively. The liquid extract was washed with 5 ml of water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (eluate: ethylacetate/n-hexane=1/4) to obtain 358 mg of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (2) as an oil. Yield 79%.

Workup

  1. wash44 mg (1.1 mmol) of 60% oil dispersion of sodium hydride was washed twice with 2 ml of dry hexane
  2. additionwas added
  3. extractionthe reaction mixture was extracted with 8 ml
  4. extractionThe liquid extract
  5. washwas washed with 5 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under vacuum
  9. customthe residue was purified by silica gel column chromatography (eluate: ethylacetate/n-hexane=1/4)

Sources & evidence

ORD record
ord-73d4b8d4d5e2426a9d4c3d10099f2f7c
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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