Triethylamine → 5-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide

HRID 49524

反応式

HRID 49524 の反応式
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=O)=[O:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[F:27][C:28]([F:38])([F:37])[C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>C(Cl)Cl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([NH:34][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:37])[F:38])=[CH:36][CH:35]=1)=[O:10])=[O:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 39266835-Formyl-2-methoxybenzoic acid

生成物 1

HCID 120946615-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 1.00 g of 5-formyl-2-methoxybenzoic acid in 50 ml of methylene chloride were added 1.00 ml of triethylamine and 0.60 ml of ethyl chlorocarbonate, and the mixture was stirred for 15 minutes at room temperature. Then, a solution of 1.17 g of 4-trifluoromethylbenzylamine in 10 ml of methylene chloride was added and the mixture was stirred further for 3 hours at room temperature. After washed with water, the reaction mixture was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue obtained was purified by means of column chromatography (silica gel, hexane:ethyl acetate=1:1) and then recrystallized from a mixed solvent of diethyl ether-ethyl acetate-hexane to obtain 1.46 g of 5-formyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.

後処理

  1. stirringthe mixture was stirred further for 3 hours at room temperature
  2. washAfter washed with water
  3. dry with materialthe reaction mixture was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. customwas purified by means of column chromatography (silica gel, hexane:ethyl acetate=1:1)
  7. customrecrystallized from a mixed solvent of diethyl ether-ethyl acetate-hexane

出典と根拠

ORDレコード
ord-85c9d352781a4a668ba10aa38b2d8687
出典データセット
uspto-grants-2004_03
特許番号
US06706763B1

関連ノート

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