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

HRID 351178

반응식

HRID 351178 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-263aa6ba2d364930bfb76f9c2d88b47f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183273B2

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