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

HRID 59289

반응식

HRID 59289 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d0adaacf7d1f472794d4e88810d0c6df
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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