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

HRID 1018019ノート

反応式

HRID 1018019 の反応式
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

参加物

4

反応物 3

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

生成物 1

HCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde収率 93.4%

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2a7457bb66b94277abdbfd10b6aaffe4
出典データセット
uspto-grants-2002_11
特許番号
US06479664B1

反応ノート

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