Phenacyl bromide → HCID 178521438, compound

HRID 1067683Notes

Reaction equation

HRID 1067683 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][OH:16])[N:10]=[CH:9]2)C=CC=CC=1.Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>C(Cl)Cl>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][CH2:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:32])[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 178521438HCID 178521438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 mmol of 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanol and 5 mmol of 2-bromo-1-phenylethanone are stirred for 72 hours in methylene chloride. The solvent is evaporated off under reduced pressure and the residue is refluxed for 1 hour in 30 ml of 2N HCl and 30 ml of acetone. The solvent is evaporated off under reduced pressure and triphenylmethanol is extracted using diethyl ether. The aqueous phase is alkalized with ammonia, and the crude product is extracted with diethyl ether, purified by rotatory chromatography and crystallized as hydrogen maleate from diethyl ether and ethanol.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. temperaturethe residue is refluxed for 1 hour in 30 ml of 2N HCl
  3. customThe solvent is evaporated off under reduced pressure and triphenylmethanol
  4. extractionis extracted
  5. extractionthe crude product is extracted with diethyl ether
  6. custompurified by rotatory chromatography
  7. customcrystallized as hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-29924635e3794ff6b334726d05ba47e3
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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