1-Chloro-2-nitrobenzene → N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

HRID 508778

反応式

HRID 508778 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].O[CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

参加物

4

反応物 2

HCID 69451-Chloro-2-nitrobenzeneHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

生成物 1

HCID 19879857N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide収率 30,891.9%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
75 °C

実験手順

To a solution of 1-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in conc. sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80° C. for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J=3.9 Hz, 2H), 7.62-7.64 (m, 1H), 7.72-7.78 (m, 1H), 7.97-8.01 (m, 1H), 10.09 (brs, 1H).

後処理

  1. customThe reaction mass was quenched in ice cold water
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe obtained crude product
  5. customwas purified by column chromatography on silica gel eluting with 4% EtOAc

出典と根拠

ORDレコード
ord-a15ed8d195bf492bb80dad58e5f3a947
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

関連ノート

読み込み中…