Ethanol → Ethyl (4-acetyl-2-nitrophenyl)aminobenzoate

HRID 49826

反応式

HRID 49826 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:3].N[C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([N:28](CC)CC)C.C(O)C>CN1C(=O)CCC1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:28][C:23]2[CH:24]=[CH:25][CH:15]=[CH:16][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)(=[O:3])[CH3:1]

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 27346124'-Fluoro-3'-nitroacetophenone

生成物 1

HCID 53953856Ethyl (4-acetyl-2-nitrophenyl)aminobenzoate収率 938.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A mixture 1b (11.0 g, 60.2 mmol), ethyl 3-aminobenzoate (9.9 g, 6.2 mmol) and triethylamine (8.34 ml, 60.2 mmol) in anhydrous NMP (5 ml) was heated to 130° C. with stirring under a stream of nitrogen for 4 hours. The cooled mixture was poured into ice-water (100 ml). Ethanol (10 ml) was added and the mixture was stirred until crystallization was completed. The precipitate was filtered off, washed with water and dried to yield ethyl (4-acetyl-2-nitrophenyl)aminobenzoate (19.1 g, 97%). This ester was hydrogenated quantitatively in a mixture of ethanol (400 ml) and dichloromethane (100 ml) using Pd (5% on activated carbon) as the catalyst. The resulting diamine was heated to reflux in formic acid (100 ml) for 1 hour. The cooled mixture was poured into ice-water (400 ml) and the precipitate was filtered off, washed with water and dried to yield 5-acetyl-1-(3-ethoxycarbonyl)phenylbenzimidazole (16.4 g, 91%).

後処理

  1. stirringthe mixture was stirred until crystallization
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-624de12a3733497c8932b4e4bb825d7e
出典データセット
uspto-grants-2004_03
特許番号
US06710044B2

関連ノート

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