Allylamine → N-Allyl-4-oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butanamide

HRID 28335

反応式

HRID 28335 の反応式
CO[C:3](=[O:25])[CH2:4][CH2:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[CH2:26]([NH2:29])[CH:27]=[CH2:28].[Cl-].[NH4+]>>[CH2:26]([NH:29][C:3](=[O:25])[CH2:4][CH2:5][C:6](=[O:24])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:17][CH:18]=2)=[CH:11][CH:12]=1)[CH:27]=[CH2:28]

参加物

4

反応物 3

HCID 7853AllylamineHCID 25517Ammonium ChlorideHCID 11256659Methyl-4-oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butanoate

生成物 1

HCID 68931823N-Allyl-4-oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butanamide

実験手順

Methyl-4-oxo-4-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]butanoate (VIII-a-1) (18.2 g, 52 mmol) is treated with allylamine (41.6 g, 730 mmol) and ammonium chloride (1.8 g, 33 mmol) and heated under reflux for 6 h. For work-up, the mixture is poured into ice-cold aqueous HCl (2 M) and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4) and concentrated. The crude product (17.7 g, content: 84.5%, HPLC, 100% method) is recrystallized from toluene.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 6 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product (17.7 g, content: 84.5%, HPLC, 100% method) is recrystallized from toluene

出典と根拠

ORDレコード
ord-eca6187f7133485ea5fb9d59be79cc02
出典データセット
uspto-grants-2008_09
特許番号
US07419936B2

関連ノート

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