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

HRID 1723137

반응식

HRID 1723137 반응식
[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

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 81783Ethyl 2-chlorobenzoateHCID 14518433HCID 14518433, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-03ca0c695822486580ea1450ede57cce
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04859684

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