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

HRID 1018020노트

반응식

HRID 1018020 반응식
CN(C)C=[O:4].O=[C:7]([Cl:13])OC(Cl)(Cl)Cl.[CH2:14]([N:21](C=CC)C(=O)C)[C:15]1[CH:20]=C[CH:18]=[CH:17][CH:16]=1>>[Cl:13][C:7]1[C:17]([CH:18]=[O:4])=[CH:16][C:15]([CH3:20])=[CH:14][N:21]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 10426DiphosgeneHCID 53742793N-benzyl-N-(1-Propenyl)acetamide

생성물 1

HCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde수율 93.4%

반응 조건

온도
75 °C

실험 절차

Dimethylformamide (13.54 g, 0.185 moles) was added to a well stirred and cooled material of diphosgene (36.64 g, 0.185 moles) at 10° C. in 30 minutes in an ice bath followed by N-benzyl-N-(1-Propenyl)acetamide (5 g, 0.026 moles) at the same temperature. The reaction mixture was further continued for 2 hours at 25° C. The ice cold bath was removed and heated to 75° C. for 5 hours. The orange-yellow coloured organic mass was poured in ice cold water (200 g) with stirring. The mass was extracted with methylenechloride (2×200 ml) and the layer separated. The organic layer was dried over sodium sulfate, and solvent removed under reduced pressure. Residue obtained was subjected to chromatographic purification on silica gel to give 2-chloro-5-methylpyridine-3-carbaldehyde (3.78 g) in 92% yield.

후처리

  1. customThe ice cold bath was removed
  2. additionThe orange-yellow coloured organic mass was poured in ice cold water (200 g)
  3. stirringwith stirring
  4. extractionThe mass was extracted with methylenechloride (2×200 ml)
  5. customthe layer separated
  6. dry with materialThe organic layer was dried over sodium sulfate, and solvent
  7. customremoved under reduced pressure
  8. customResidue obtained
  9. customwas subjected to chromatographic purification on silica gel

출처 및 근거

ORD 기록
ord-d0b9b057720f488a9f25682d2b77664a
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479664B1

반응 노트

불러오는 중…