Dimethylformamide → 2-Chloro-5-methylpyridine-3-carbaldehyde

HRID 389264노트

반응식

HRID 389264 반응식
CN([CH:4]=[O:5])C.[CH2:6]([N:13](/C=C/C)C(=O)C)[C:7]1[CH:12]=CC=[CH:9][CH:8]=1.[C:20]([Cl:23])(Cl)=O>>[Cl:23][C:20]1[C:9]([CH:4]=[O:5])=[CH:8][C:7]([CH3:12])=[CH:6][N:13]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 6371PhosgeneHCID 9942349N-Benzyl-N-(prop-1-en-1-yl)acetamide

생성물 1

HCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

반응 조건

온도
0 °C

실험 절차

DMF (2.86 mL, 37.0 mmol) was added slowly over 2 minutes to an ice-cold solution of N-benzyl-N—((E)-propenyl)-acetamide (1.0 g, 5.3 mmol) and phosgene (20% in toluene; 18.3 mL, 37.0 mmol). After stirring for 30 minutes at 0° C., the ice bath was removed, and the reaction was stirred at room temperature for 2 hours, and then heated to 75° C. for 4.5 hours. The mixture was poured over ice and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

후처리

  1. customthe ice bath was removed
  2. stirringthe reaction was stirred at room temperature for 2 hours
  3. temperatureheated to 75° C. for 4.5 hours
  4. additionThe mixture was poured over ice
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a649daeb1e954ae581ea45ca6a209bd6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378107B2

반응 노트

불러오는 중…