Dimethylformamide → 3-Chloro-2-methyl-6-nitrobenzonitrile

HRID 322006

反応式

HRID 322006 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12].[C:13]([Cu])#[N:14].CN(C=O)C>C(OCC)(=O)C>[Cl:11][C:4]1[C:3]([CH3:12])=[C:2]([C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[C:13]#[N:14]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 971552,6-Dichloro-3-nitrotolueneHCID 178418546HCID 178418546、化合物2 回

生成物 1

HCID 220089613-Chloro-2-methyl-6-nitrobenzonitrile収率 60.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 10 g (49 mmol) of 2,6-dichloro-3-nitrotoluene and 4.8 g (54.0 mmol) of CuCN in 100 ml of abs. DMF was stirred at 150° C. for 6 h, a further 2.4 g (27.0 mmol) of CuCN being added after 4 h. The solvent was stripped off and the residue obtained taken up in ethyl acetate. The precipitate deposited was filtered off and extracted several times with warm ethyl acetate. The combined ethyl acetate solutions were washed with H2O, dilute ammonia solution, and saturated NaCl solution, dried over Na2SO4, and concentrated to dryness. The resulting yellow, crystalline residue was purified by column chromatography on SiO2 using EA/n-heptane 1:10 as a solvent. 5.8 g of the title compound resulted in the form of yellow crystals.

後処理

  1. customthe residue obtained
  2. filtrationThe precipitate deposited was filtered off
  3. extractionextracted several times with warm ethyl acetate
  4. washThe combined ethyl acetate solutions were washed with H2O, dilute ammonia solution, and saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe resulting yellow, crystalline residue was purified by column chromatography on SiO2

出典と根拠

ORDレコード
ord-dee4e1ef582640dcb0215f4430dde985
出典データセット
uspto-grants-2001_04
特許番号
US06211196B1

関連ノート

読み込み中…