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

HRID 1018019노트

반응식

HRID 1018019 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 4° 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 was separated. The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue 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 was separated
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained residue was subjected to chromatographic purification on silica gel

출처 및 근거

ORD 기록
ord-2a7457bb66b94277abdbfd10b6aaffe4
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479664B1

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