Toluene → HCID 9870921, compound

HRID 609770Notes

Reaction equation

HRID 609770 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([O:20]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]1([CH2:28][CH2:29][CH2:30][N:31]2[C:39]3[C:34](=[CH:35][C:36]([NH2:40])=[CH:37][CH:38]=3)[CH:33]=[CH:32]2)[CH:27]=[CH:26][N:25]=[CH:24]1.C[O-].[Na+].C1(C)C=CC=CC=1>CO>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([NH:40][C:36]1[CH:35]=[C:34]2[C:39](=[CH:38][CH:37]=1)[N:31]([CH2:30][CH2:29][CH2:28][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)[CH:32]=[CH:33]2)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 196003931-[3-(1H-Imidazol-1-yl)propyl]-1H-indol-5-amineHCID 19600418HCID 19600418, compound

Product 1

HCID 9870921HCID 9870921, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 27.9 g of ethyl 1-benzyl-6-chlorobenzimidazol-2-carboxylate, 17.8 g of 1-[3-(imidazol-1-yl)propyl]-5-aminoindole, 8 g of sodium methylate and 600 ml of toluene was stirred at 100° C. for 1.5 hours. The reaction mixture was cooled to room temperature, the crystals being separated were collected by filtration and washed with toluene. Thus obtained crystals were dissolved in 500 ml of chloroform, then 100 ml of water was added and the mixture was filtrated with Celite. The chloroform layer was taken by separation, after washed with water, the chloroform portion layer was dried with anhydrous magnesium sulfate, and the solvent was removed by distillation to obtain brown oily product. This oily product was dissolved in methanol, further added n-hexane and the crystals being separated were collected by filtration, recrystallized from methanol and dried. There was obtained 31.8 g of 1-benzyl-6-chloro-2-{1-[3-(imidazol-1-yl)propyl]indol-5-ylamino-carbonyl}benzimidazole.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe crystals being separated
  3. filtrationwere collected by filtration
  4. washwashed with toluene
  5. dissolutionThus obtained crystals were dissolved in 500 ml of chloroform
  6. addition100 ml of water was added
  7. filtrationthe mixture was filtrated with Celite
  8. customThe chloroform layer was taken by separation
  9. washafter washed with water
  10. dry with materialthe chloroform portion layer was dried with anhydrous magnesium sulfate
  11. customthe solvent was removed by distillation
  12. customto obtain brown oily product
  13. customfurther added n-hexane and the crystals being separated
  14. filtrationwere collected by filtration
  15. customrecrystallized from methanol
  16. customdried

Sources & evidence

ORD record
ord-de94bc4868ba4d15b23d3809bbef9b28
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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