Trimethyl orthoformate → HCID 178478069, compound

HRID 1723138Notes

Reaction equation

HRID 1723138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22]OC(OC)OC>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:14]=[CH:13][C:12]3[NH:15][CH:22]=[N:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 14500563HCID 14500563, compound

Product 1

HCID 178478069HCID 178478069, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2.99 parts of 4-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-1,2-benzenediamine, 50 parts of trimethoxymethane and 2.4 parts of formic acid was stirred for 16 hours at room temperature. The reaction mixture was evaporated. The residue was dissolved in hydrochloric acid solution 2N. This 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, yielding 1.8 parts (58.2%) of 5-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-benzimidazole; mp. 108.2° C. (compound 93).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in hydrochloric acid solution 2N
  3. additionThis solution was treated with ammonia
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane, methanol and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-510e8ec0aa8c41238c92e254db3cb721
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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