Chloroacetic Acid → 2-(Chloromethyl)-5,6-dimethyl-1h-benzimidazole

HRID 351178

反応式

HRID 351178 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[Cl:11][CH2:12][C:13](O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[Cl:11][CH2:12][C:13]1[NH:9][C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=2[N:10]=1

参加物

6

反応物 3

HCID 300Chloroacetic AcidHCID 10340Sodium CarbonateHCID 766354,5-Dimethyl-1,2-phenylenediamine

生成物 1

HCID 2662802-(Chloromethyl)-5,6-dimethyl-1h-benzimidazole収率 54.5%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

実験手順

To a stirred solution of 4,5-dimethylphenylene-1,2-diamine (680 mg, 5 mmol) in 4N HCl (12 mL) was added chloroacetic acid (940 mg, 10 mmol). The solution was then heated to reflux for 17 hours, then cooled to room temperature. Solid sodium carbonate was then added slowly, with stirring, until the pH of the solution was approximately 9.0, at which point a beige precipitate formed. The aqueous phase was then diluted with water (10 mL) and extracted repeatedly with ethyl acetate. The combined organic fractions were then dried, concentrated and the residue was purified by column chromatography on silica gel (10% MeOH in CH2Cl2) to afford the desired 2-(chloromethyl)-5,6-dimethylbenzimidazole (530 mg, 54%). 1H NMR (CDCl3) δ 1.59 (br s, 1H), 2.31 (s, 6H), 4.83 (s, 2H), 7.42 (s, 2H).

後処理

  1. temperatureThe solution was then heated
  2. temperatureto reflux for 17 hours
  3. customat which point a beige precipitate formed
  4. extractionextracted repeatedly with ethyl acetate
  5. customThe combined organic fractions were then dried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography on silica gel (10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-263aa6ba2d364930bfb76f9c2d88b47f
出典データセット
uspto-grants-2007_02
特許番号
US07183273B2

関連ノート

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