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

HRID 13854

반응식

HRID 13854 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 206446982-[Methyl(phenylmethyl)amino]acetaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

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 MgSO4 and filtered to provide the title compound which was used without further purification.

후처리

  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 MgSO4
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-91e1be0e020040e7aa4ba5c2fabcadab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728144B2

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