Hydrochloric Acid → 5-(1H-imidazol-1-ylmethyl)-2-(3-thienyl)-1H-benzimidazole dihydrochloride

HRID 1723147노트

반응식

HRID 1723147 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.[S:15]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16]1.[ClH:22].[OH-].[NH4+]>>[ClH:22].[ClH:22].[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]3[NH:13][C:20]([C:17]4[CH:18]=[CH:19][S:15][CH:16]=4)=[N:14][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 145184334-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine

생성물 1

HCID 1784785545-(1H-imidazol-1-ylmethyl)-2-(3-thienyl)-1H-benzimidazole dihydrochloride수율 8.5%

실험 절차

A mixture of 5 parts of 4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 3 parts of 3-thiophenecarboxaldehyde and 50 parts of a hydrochloric acid solution 3N was stirred for 36 hours at reflux temperature. After cooling, the mixture was poured into 100 parts of crushed ice and ammonium hydroxide. The product was extracted three times with 75 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 (90:10:0.1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 8 parts of 2-propanone and ethanol at 0° C. The salt was filtered off and crystallized from a mixture of methanol and 2-propanone. The product was filtered off and dried, yielding 0.8 parts (8.5%) of 5-(1H-imidazol-1-ylmethyl)-2-(3-thienyl)-1H-benzimidazole dihydrochloride; mp.>300° C. (dec.) (compound 205).

후처리

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionThe product was extracted three times with 75 parts of trichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (HPLC) over silica gel using
  8. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customwas converted into the hydrochloride salt in 8 parts of 2-propanone and ethanol at 0° C
  12. filtrationThe salt was filtered off
  13. customcrystallized from a mixture of methanol and 2-propanone
  14. filtrationThe product was filtered off
  15. customdried

출처 및 근거

ORD 기록
ord-01e473e282f54e2aaf37231638f11c5d
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04859684

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