Triethylamine → 2-Methoxy-5-nitro-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide

HRID 1634518ノート

反応式

HRID 1634518 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.C(Cl)(=O)OCC.[F:28][C:29]([F:39])([F:38])[C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>ClCCl.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([NH:35][CH2:34][C:33]1[CH:32]=[CH:31][C:30]([C:29]([F:28])([F:38])[F:39])=[CH:37][CH:36]=1)=[O:7]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 2841632-Methoxy-5-nitrobenzoic acid

生成物 1

HCID 110573402-Methoxy-5-nitro-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide収率 77.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Publicly known [e.g. De.Paulis et al, J. Med. Chem., 1022(1922)]2-methoxy-5-nitrobenzoic acid (9.00 g, 45.7 mmol) was dissolved in 450 ml of dichloromethane and, after triethylamine (8.11 ml, 58.4 mmol) and ethyl chlorocarbonate (4.70 ml, 49.3 mmol) were added, the mixture was stirred for 45 minutes at room temperature. Next, 4-trifluoromethylbenzylamine (9.59 g, 54.8 mmol) was added dropwise, which was stirred for 30 minutes at room temperature. The reaction mixture was poured into water. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate to obtain 12.5 g of the aimed compound as yellow powder. Further, the filtrate was concentrated and recrystallized from ethyl acetate to obtain 2.13 g of the second crystals. Total 14.6 g (91%).

後処理

  1. stirringwhich was stirred for 30 minutes at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-15d99f8ddd9f4df4a8211127c2efebb8
出典データセット
uspto-grants-2003_01
特許番号
US06506797B1

反応ノート

読み込み中…