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

HRID 1018021ノート

反応式

HRID 1018021 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 (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.

後処理

  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

出典と根拠

ORDレコード
ord-0ba8bf2ce7a84cafb662289fc729be90
出典データセット
uspto-grants-2002_11
特許番号
US06479664B1

反応ノート

読み込み中…