Dimethylformamide → 1H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

HRID 1756818ノート

反応式

HRID 1756818 の反応式
CN(C)[CH:3]=[O:4].[CH2:6]([C:9]1[NH:13][C:12](=O)[CH2:11][N:10]=1)[CH2:7][CH3:8].O=P(Cl)(Cl)[Cl:17].[OH-].[Na+]>ClC1C=CC=CC=1>[CH2:6]([C:9]1[NH:13][C:12]([Cl:17])=[C:11]([CH:3]=[O:4])[N:10]=1)[CH2:7][CH3:8]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 193917563,5-Dihydro-2-propyl-4H-imidazol-4-one

生成物 1

HCID 97939751H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-収率 45.4%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
100 °C

実験手順

N,N-dimethylformamide (7.04 g, 96.3 mmol) was added to a mixture of 2-n-propyl-3,5-dihydroimidazol-4-one (4.49 g, 35.6 mmol) and POCl3 (14.76 g, 96.3 mmol) in chlorobenzene (40 ml) at 100° C. The mixture was heated for 2 hours at 100° C., cooled and poured on 40 g of ice. The mixture was adjusted to pH 1 by the addition of 30 percent sodium hydroxide solution (22.5 ml) and the phases were separated. The aqueous phase was extracted twice with 40 ml of ethyl acetate each and the combined organic phases were washed with water (20 ml) and filtered on silica gel. After removal of the solvent from the filtrate, 2.79 g of a light brown solid was obtained. Recrystallization from ethyl acetate/petroleum ether yielded the title compound (2.04 g, 33 percent). The product had a melting point of 133.3° to 137.5° C. Other data concerning the product was:

後処理

  1. temperaturecooled
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted twice with 40 ml of ethyl acetate each and the combined organic phases
  4. washwere washed with water (20 ml)
  5. filtrationfiltered on silica gel
  6. customAfter removal of the solvent from the filtrate

出典と根拠

ORDレコード
ord-66012a0783994fe4995cf5617782da19
出典データセット
uspto-grants-1995_08
特許番号
US05442075

反応ノート

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