1-Bromo-3-chloropropane → 5-chloro-1-(3-chloropropyl)-1,3-dihydro-3-phenyl-2H-benzimidazol-2-one

HRID 354919

反応式

HRID 354919 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:17]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:21][CH2:22][CH2:23][Cl:24])[C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:17]=1

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1086532H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-phenyl-

生成物 1

HCID 205063095-chloro-1-(3-chloropropyl)-1,3-dihydro-3-phenyl-2H-benzimidazol-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 7 parts of 6-chloro-1,3-dihydro-1-phenyl-2H-benzimidazol-2-one in 67.5 parts of N,N-dimethylformamide is added portionwise 1 part of a sodium hydride dispersion 78%. After stirring for 2 hours at room temperature, there are added dropwise (slowly) 4.75 parts of 1-bromo-3-chloropropane. Upon completion, stirring is continued first for two hours at room temperature and further for one hour at 60° C. The reaction mixture is poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5-chloro-1-(3-chloropropyl)-1,3-dihydro-3-phenyl-2H-benzimidazol-2-one as a residue.

後処理

  1. stirringUpon completion, stirring
  2. waitis continued first for two hours at room temperature and further for one hour at 60° C
  3. additionThe reaction mixture is poured onto water
  4. extractionthe product is extracted with methylbenzene
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and 5% of methanol as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated

出典と根拠

ORDレコード
ord-15485e61d700424bb74f4a12031fe126
出典データセット
uspto-grants-1983_03
特許番号
US04377578

関連ノート

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