Chloroacetic Acid → 2-(Chloromethyl)-1-methylbenzimidazole

HRID 495255

反応式

HRID 495255 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-])=O.[H][H].[Cl:14][CH2:15][C:16](O)=O.Cl.C(=O)(O)[O-].[Na+]>[Pd].O.C(O)C>[Cl:14][CH2:15][C:16]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=1

参加物

9

反応物 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 69157Benzenamine, N-methyl-2-nitro-HCID 516892Sodium BicarbonateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 2480442-(Chloromethyl)-1-methylbenzimidazole収率 77.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a pressure reaction bottle was added 4 g N-methyl-2-nitroaniline, 0.44 g 5% palladium on carbon, and 100 ml ethanol. The mixture was hydrogenated at 22 C and 40 psi hydrogen for 2 hours. Following filtration through celite, and solvent removal, a dark red oil was obtained. To this oil was added 3.7 g chloroacetic acid and 40 ml 5M hydrochloric acid. After refluxing under nitrogen for 2.5 hours, the mixture was cooled to 22 C, diluted with 200 ml water, and neutralized with solid sodium bicarbonate. The resulting solid was filtered, washed with water and dried giving 3.7 g gray solid.

後処理

  1. customTo a pressure reaction bottle
  2. filtrationfiltration
  3. customthrough celite, and solvent removal
  4. customa dark red oil was obtained
  5. temperatureAfter refluxing under nitrogen for 2.5 hours
  6. temperaturethe mixture was cooled to 22 C
  7. filtrationThe resulting solid was filtered
  8. washwashed with water
  9. customdried

出典と根拠

ORDレコード
ord-85cb25830ff741ebbf8f07b571cd5dc8
出典データセット
uspto-grants-2009_05
特許番号
US07538931B2

関連ノート

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