Trimethyl orthoformate → HCID 178420194, compound

HRID 1723139Notes

Reaction equation

HRID 1723139 reaction equation
[N:1]1([CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[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.[CH3:21]OC(OC)OC>C(O)(=O)C>[N:1]1([CH:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]2[CH:12]=[CH:11][C:10]3[NH:13][CH:21]=[N:14][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 14990928HCID 14990928, compound

Product 1

HCID 178420194HCID 178420194, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.64 parts of 4-[(1H-imidazol-1-yl)phenylmethyl]-1,2-benzenediamine, 50 parts of trimethoxymethane and 1.2 parts of acetic acid was stirred and refluxed for 8 hours. The reaction mixture was evaporated in vacuo. The residue was dissolved in dilute hydrochloric acid. The solution was treated with ammonia and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (90:5:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The solid residue was washed with 2-propanone, yielding 1.8 parts (65%) of 5-[(1H-imidazol-1-yl)phenylmethyl]-1H-benzimidazole; mp. 186.2° C. (compound 111).

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dilute hydrochloric acid
  4. additionThe solution was treated with ammonia
  5. extractionthe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane, methanol and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. washThe solid residue was washed with 2-propanone

Sources & evidence

ORD record
ord-defaf82158d342ff84fb1b31cb7f1c5f
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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