Acetic Acid → HCID 14518527, compound

HRID 1723141Notes

Reaction equation

HRID 1723141 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH2:21])[C:10]([NH:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:22](OC(OCC)(OCC)C)[CH3:23].C(O)(=O)C>CO>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]3[N:13]([CH2:14][C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[C:22]([CH3:23])=[N:21][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 54395078HCID 54395078, compound

Product 1

HCID 14518527HCID 14518527, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.6 parts of 4-(1H-imidazol-1-ylmethyl)-N1 -(3-pyridinylmethyl)-1,2-benzenediamine, 20 parts of triethoxyethane, 2 parts of acetic acid and 200 parts of methanol was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated. Methanol and methanol, saturated with ammonia, were added. The mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (88:10:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 40 parts of 4-methyl-2-pentanone. The product was filtered off and dried, yielding 2.5 parts (41%) of 5-(1H-imidazol-1-yl-methyl)-2-methyl-1-(3-pyridinylmethyl)-1H-benzimidazole; mp. 174.0° C. (compound 116).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionMethanol and methanol, saturated with ammonia, were added
  4. customThe mixture was evaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane, methanol and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 40 parts of 4-methyl-2-pentanone
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-2ca2c11b638e49bca1b119e7e262961f
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

Loading…