Ammonium Hydroxide → 2-(2-chlorophenyl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole

HRID 1723137

反応式

HRID 1723137 の反応式
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1[C:18](OCC)=O.[OH-].[NH4+]>O>[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1[C:18]1[NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:8][C:9]=2[N:14]=1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 81783Ethyl 2-chlorobenzoateHCID 14518433HCID 14518433、化合物

生成物 1

HCID 1784780202-(2-chlorophenyl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole収率 26%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture of 5 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 5 parts of ethyl 2-chlorobenzoate and 30 parts of polyphosphoric acid was stirred for 4 hours at 140° C. The whole was poured into 200 parts of water and crushed ice. The mixture was treated with ammonium hydroxide. The product was extracted three times with 120 parts of trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (HPLC) over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.05 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane. The product was filtered off and dried in vacuo at 100° C., yielding 2.1 parts (26%) of 2-(2-chlorophenyl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole; mp. 115.2° C. (compound 88).

後処理

  1. customcrushed ice
  2. extractionThe product was extracted three times with 120 parts of trichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (HPLC) over silica gel using
  7. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.05 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
  11. filtrationThe product was filtered off
  12. customdried in vacuo at 100° C.

出典と根拠

ORDレコード
ord-03ca0c695822486580ea1450ede57cce
出典データセット
uspto-grants-1989_08
特許番号
US04859684

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