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

HRID 1018021노트

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HRID 1018021 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 (19.34 g, 0.264 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 30° C. The ice cold both was removed and heated to 75° C. for 8 hours. Work up procedure was carried out according to the procedure of example 1. Before that excess DMF 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 both was removed
  2. customBefore that excess DMF was removed under reduced pressure
  3. customThe obtained residue was subjected to chromatographic purification on silica gel

출처 및 근거

ORD 기록
ord-0ba8bf2ce7a84cafb662289fc729be90
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479664B1

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