Aminoacetaldehyde dimethyl acetal → 2-(3-nitrophenyl)-1H-imidazole

HRID 322064ノート

反応式

HRID 322064 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[NH:10])OC)([O-:3])=[O:2].CO[CH:16](OC)[CH2:17][NH2:18]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[NH:18][CH:17]=[CH:16][N:10]=2)[CH:11]=[CH:12][CH:13]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 122008323-nitro-benzimidic acid methyl ester

生成物 1

HCID 8210012-(3-nitrophenyl)-1H-imidazole収率 48.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A stirred solution of methyl 3-nitrobenzimidate (7.57 g) and aminoacetaldehyde dimethylacetal (5.57 g) in methanol (20 ml) is heated under reflux for 24 hours. The cool solution is evaporated, and the residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil). The mixture is heated (steam bath) for 15 minutes and evaporated under reduced pressure. Water (50 ml) is added to the residue and the insoluble solid filtered and washed with water. The filtrate is neutralized with potassium carbonate solution and the precipitated solid filtered and washed with water. The combined solids are charcoaled and recrystallised from ethanol to give 3.87 g of 2-(3nitrophenyl)imidazole, mp 193-194.5° C.

後処理

  1. temperatureunder reflux for 24 hours
  2. customThe cool solution is evaporated
  3. additionthe residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil)
  4. temperatureThe mixture is heated (steam bath) for 15 minutes
  5. customevaporated under reduced pressure
  6. additionWater (50 ml) is added to the residue
  7. filtrationthe insoluble solid filtered
  8. washwashed with water
  9. filtrationthe precipitated solid filtered
  10. washwashed with water
  11. customrecrystallised from ethanol

出典と根拠

ORDレコード
ord-c2438538b363415a82764565feb8661b
出典データセット
uspto-grants-2001_04
特許番号
US06211220B1

反応ノート

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