Dimethylformamide → HCID 178509931、化合物

HRID 505550ノート

反応式

HRID 505550 の反応式
Br[C:2]1[C:3]([Cl:20])=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:14]2[N:13]=[N:12][NH:11][C:10]=2[CH:9]=[CH:8][C:7]=1[Cl:15].[CH3:21][N:22](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[Cl:20][C:3]1[C:4]([O:5][C:6]2[C:14]3[N:13]=[N:12][NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[Cl:15])=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=1[C:21]#[N:22]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 178477834HCID 178477834、化合物

生成物 1

HCID 178509931HCID 178509931、化合物

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 8857Ethyl Acetate溶媒

実験手順

4-(3-bromo-2,5-dichlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole (2.55 g, 6.49 mmol), tetrakis triphenylphosphine palladium(0) (2.25 g, 1.95 mmol) and zinc cyanide (0.915 g, 7.79 mmol) were suspended in dry DMF (50 mL) under N2 and placed in an oil bath at 90° C. for 24 hours, after which the reaction mixture was allowed to cool to room temperature. The cooled mixture was then diluted with EtOAc (200 mL) and washed with water (4×100 mL), the aqueous layer was extracted with EtOAc (100 mL) and then washed with water (4×50 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated with silica gel. The concentrate was purified by automated column chromatography on silica gel (40 g) eluting with 0-30% EtOAc/hexanes to afford the title compound. LRMS (M+1)=340.16.

後処理

  1. washwashed with water (4×100 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  3. washwashed with water (4×50 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated with silica gel
  7. customThe concentrate was purified by automated column chromatography on silica gel (40 g)
  8. washeluting with 0-30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-30787141399f4238aa026f88c4c05177
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

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