Dimethylformamide → 3-cyano-N, 4-dimethylbenzamide

HRID 1830878

반응식

HRID 1830878 반응식
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>N.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6])#[N:14]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 196884403-iodo-N,4-dimethylbenzamide

생성물 1

HCID 178597803-cyano-N, 4-dimethylbenzamide

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 18464838Ammonia ethyl acetate용매

반응 조건

온도
120 °C

실험 절차

3-Iodo-N, 4-dimethylbenzamide (772 mg), tetrakistriphenylphosphinepalladium (30 mg) and zinc cyanide (250 mg) were suspended in DMF (10 ml) under a nitrogen atmosphere, and the mixture was stirred at 120° C. for 12 hrs. The reaction mixture was diluted with 5% aqueous ammonia-ethyl acetate and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification. The eluate was recrystallized from ethyl acetate-hexane to give the title compound (300 mg) as colorless powder crystals.

후처리

  1. washthe organic layer was washed with water and saturated brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification
  5. customThe eluate was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-16e76a07791f45ecb4f4c029730a3c4b
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067537B2

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