4-Methyl-1-trityl-1H-imidazole → Methyl 5-(1-cyano-1-methylethyl)-3-(5-methylimidazol-1-ylmethyl)benzoate

HRID 1636797Notes

Reaction equation

HRID 1636797 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([C:16]#[N:17])([CH3:15])[CH3:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:18][C:19]1[N:20]=[CH:21][N:22](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:23]=1>C(#N)C>[C:16]([C:13]([C:11]1[CH:12]=[C:3]([CH2:2][N:20]2[C:19]([CH3:18])=[CH:23][N:22]=[CH:21]2)[CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])([CH3:15])[CH3:14])#[N:17]

Participants

4

Reactant 2

HCID 6182544-Methyl-1-trityl-1H-imidazoleHCID 19349443Methyl 3-(bromomethyl)-5-(2-cyanopropan-2-yl)benzoate

Product 1

HCID 19349403Methyl 5-(1-cyano-1-methylethyl)-3-(5-methylimidazol-1-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-bromomethyl-5-(1-cyano-1-methylethyl)benzoate (0.7 g), 4-methyl-1-tritylimidazole (0.8 g) and acetonitrile (2 ml) was heated under reflux for 48 h, then evaporated to dryness. The residue of 3-[3-(1-cyano-1-methylethyl)-5-methoxycarbonylbenzyl]-4-methyl-1-tritylimi dazolium bromide was washed with diethyl ether (2×10 ml), and the residue was treated with glacial acetic acid (4 ml) and water (1 ml) and heated at 90° for 15 minutes. The mixture was diluted with water (20 ml), and washed with diethyl ether, and the aqueous phase was basified with 10N aqueous sodium hdroxide and extracted three times with ethyl acetate. The extracts were combined and evaporated to dryness, and the residue was purified by flash column chromatography, eluting with methanol:chloroform (1:49 by volume), to give methyl 5-(1-cyano-1-methylethyl)-3-(5-methylimidazol-1-ylmethyl)benzoate, mp 101°-104°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. customevaporated to dryness
  4. washThe residue of 3-[3-(1-cyano-1-methylethyl)-5-methoxycarbonylbenzyl]-4-methyl-1-tritylimi dazolium bromide was washed with diethyl ether (2×10 ml)
  5. additionthe residue was treated with glacial acetic acid (4 ml) and water (1 ml)
  6. temperatureheated at 90° for 15 minutes
  7. additionThe mixture was diluted with water (20 ml)
  8. washwashed with diethyl ether
  9. extractionextracted three times with ethyl acetate
  10. customevaporated to dryness
  11. customthe residue was purified by flash column chromatography
  12. washeluting with methanol:chloroform (1:49 by volume)

Sources & evidence

ORD record
ord-d2d6812ff3d34892af6a204ab44e07ff
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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