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

HRID 389264ノート

反応式

HRID 389264 の反応式
CN([CH:4]=[O:5])C.[CH2:6]([N:13](/C=C/C)C(=O)C)[C:7]1[CH:12]=CC=[CH:9][CH:8]=1.[C:20]([Cl:23])(Cl)=O>>[Cl:23][C:20]1[C:9]([CH:4]=[O:5])=[CH:8][C:7]([CH3:12])=[CH:6][N:13]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 6371PhosgeneHCID 9942349N-Benzyl-N-(prop-1-en-1-yl)acetamide

生成物 1

HCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

反応条件

温度
0 °C

実験手順

DMF (2.86 mL, 37.0 mmol) was added slowly over 2 minutes to an ice-cold solution of N-benzyl-N—((E)-propenyl)-acetamide (1.0 g, 5.3 mmol) and phosgene (20% in toluene; 18.3 mL, 37.0 mmol). After stirring for 30 minutes at 0° C., the ice bath was removed, and the reaction was stirred at room temperature for 2 hours, and then heated to 75° C. for 4.5 hours. The mixture was poured over ice and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

後処理

  1. customthe ice bath was removed
  2. stirringthe reaction was stirred at room temperature for 2 hours
  3. temperatureheated to 75° C. for 4.5 hours
  4. additionThe mixture was poured over ice
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a649daeb1e954ae581ea45ca6a209bd6
出典データセット
uspto-grants-2013_02
特許番号
US08378107B2

反応ノート

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