Triphenylcarbinol → 2-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

HRID 1795257Notes

Reaction equation

HRID 1795257 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1.[Cu][C:33]#[N:34].C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[C:13]([N:11]1[CH:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:33]#[N:34])[N:9]=[CH:10]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 6457TriphenylcarbinolHCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 221851592-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-bromo-phenyl)-1-trityl-1H-imidazole (73.0 g, 163.3 mmol) in dimethylformamide (500 ml) was added copper (I) cyanide (17.5 g, 195.9 mmol). The reaction was heated to ˜80° C. under nitrogen for 14 h. After cooling to about 50° C., the reaction was diluted with toluene (ca. 300 ml) and slowly poured onto ammonium hydroxide (3N, 1.5 L) while stirring vigorously. The mixture was stirred for 40 min and then filtered in vacuo over a bed of celite (slow filtration, required ˜2 h). The phases were separated and the organic layer was washed with brine (75 ml×3) and dried (sodium sulfate). Concentration of the solvent afforded a light brown solid. The crude product contains ˜10–15% of trityl alcohol (by HPLC) and was used without further purification in the subsequent step.

Workup

  1. temperatureAfter cooling to about 50° C.
  2. additionslowly poured onto ammonium hydroxide (3N, 1.5 L)
  3. stirringThe mixture was stirred for 40 min
  4. filtrationfiltered in vacuo over a bed of celite (
  5. filtrationslow filtration
  6. custom˜2 h
  7. customThe phases were separated
  8. washthe organic layer was washed with brine (75 ml×3)
  9. dry with materialdried (sodium sulfate)
  10. customConcentration of the solvent afforded a light brown solid
  11. customwas used without further purification in the subsequent step

Sources & evidence

ORD record
ord-6268f68576ce443bb9613929eb45e039
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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