4-(Bromomethyl)benzonitrile → 3-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

HRID 2290561Notes

Reaction equation

HRID 2290561 reaction equation
CN(C)C([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][Si](C)(C)C)[N:7]=[CH:6]1)=O.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1>C(#N)C.Cl>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:7]2[C:8]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:9][N:5]=[CH:6]2)=[CH:22][CH:23]=1)#[N:28]

Participants

5

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Product 1

HCID 136882083-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 97.0 g of 1-dimethylcarbamoyl-4-trimethylsilyloxypropyl-1H-imidazole and 72.0 g of 1-bromomethyl-4-cyanobenzene in 500 ml of acetonitrile is refluxed for 10 hours. The solution is cooled to 0° in an ice bath and ammonia gas is bubbled in for a few minutes. The mixture is then evaporated in vacuo to give a semi-solid which is dissolved in 500 ml of 1N hydrochloric acid. The solution is allowed to stand at room temperature for 15 minutes and then is extracted with ether. The pH of the aqueous phase is adjusted to 9 with 50% sodium hydroxide solution and the mixture is then extracted with methylene chloride. The methylene chloride extracts are washed with water, dried over sodium sulfate and evaporated to give a semi-solid which is triturated with cold acetone to yield the title compound (b) as a white solid, m.p. 121°-123°.

Workup

  1. temperatureThe solution is cooled to 0° in an ice bath
  2. customammonia gas is bubbled in for a few minutes
  3. customThe mixture is then evaporated in vacuo
  4. customto give a semi-solid which
  5. extractionis extracted with ether
  6. extractionthe mixture is then extracted with methylene chloride
  7. washThe methylene chloride extracts are washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customto give a semi-solid which
  11. customis triturated with cold acetone

Sources & evidence

ORD record
ord-98b5e1f5af734ababdd5b851c0896a06
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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