Dimethylformamide → 3-cyano-N, 4-dimethylbenzamide

HRID 1830878

反応式

HRID 1830878 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 178597803-cyano-N, 4-dimethylbenzamide

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 18464838Ammonia ethyl acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-16e76a07791f45ecb4f4c029730a3c4b
出典データセット
uspto-grants-2006_06
特許番号
US07067537B2

関連ノート

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