N,N-Diethylaniline → 2-Chloro-5-fluoro-1-methyl-1H-benzimidazole

HRID 330890ノート

反応式

HRID 330890 の反応式
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=O)[NH:8][C:4]=2[CH:3]=1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:7]1[N:6]([CH3:10])[C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=2[N:8]=1

参加物

4

反応物 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 220286845-Fluoro-1-methyl-1H-benzo[d]imidazol-2(3H)-one

生成物 1

HCID 219858282-Chloro-5-fluoro-1-methyl-1H-benzimidazole

実験手順

3.9 g 5-fluoro-1-methyl-1,3-dihydro-benzimidazole-2-one are suspended in 80 ml phosphorus oxychloride and the reaction mixture is stirred for 2 hours at reflux temperature. 50 ml diethylaniline are added. The reaction mixture is stirred for a further 10 minutes at reflux temperature and slowly mixed with ice water. The product is extracted with dichloromethane and purified by chromatography (silica gel, cyclohexane, methylene chloride/acetone 20/1). 1.4 g product are obtained as a solid. M.p=138-141° C.

後処理

  1. temperatureat reflux temperature
  2. stirringThe reaction mixture is stirred for a further 10 minutes
  3. temperatureat reflux temperature
  4. extractionThe product is extracted with dichloromethane
  5. custompurified by chromatography (silica gel, cyclohexane, methylene chloride/acetone 20/1)

出典と根拠

ORDレコード
ord-63def6587a5147a080780e1f402f7636
出典データセット
uspto-grants-2014_11
特許番号
US08877758B2

反応ノート

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