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

HRID 322006

반응식

HRID 322006 반응식
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]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 971552,6-Dichloro-3-nitrotolueneHCID 178418546HCID 178418546, 화합물2회

생성물 1

HCID 220089613-Chloro-2-methyl-6-nitrobenzonitrile수율 60.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dee4e1ef582640dcb0215f4430dde985
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211196B1

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