Dimethyl Sulfoxide → 2-[Methyl(phenylmethyl)amino]acetaldehyde

HRID 924636Notes

Reaction equation

HRID 924636 reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH:10]=[O:11])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 66876N-Benzyl-N-methylethanolamineHCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridine

Product 1

HCID 206446982-[Methyl(phenylmethyl)amino]acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a 3-necked 2-L flask was added N-benzyl-N-methylethanolamine (30.5 g, 0.182 mol), DCM (0.5 L), DIPEA (95 mL, 0.546 mol) and DMSO (41 mL, 0.728 mol). Using an ice bath, the mixture was cooled to about −10° C. and sulfur trioxide pyridine-complex (87 g, 0.546 mol) was added in 4 portions over 5 minute intervals. The reaction was stirred at −10° C. for 2 hours. Before removing the ice-bath, the reaction was quenched by adding water (0.5 L). The aqueous layer was separated and the organic layer was washed with water (0.5 L) and brine (0.5 L) and then dried over magnesium sulfate and filtered to provide the title compound which was used without further purification.

Workup

  1. customBefore removing the ice-bath
  2. customthe reaction was quenched
  3. additionby adding water (0.5 L)
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with water (0.5 L) and brine (0.5 L)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3f9e9d5c8397421f84d7c4493ee8bcbc
Source dataset
uspto-grants-2016_03
Patent number
US09283183B2

Reaction notes

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