4-Bromobenzyl bromide → Ammonium Hydroxide

HRID 477988

Reaction equation

HRID 477988 reaction equation
C[N:2](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:4].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C(#N)C>[NH4+:2].[OH-:4].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:7]2[C:8]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:9][N:5]=[CH:6]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Product 2

HCID 14923Ammonium HydroxideHCID 224668773-[1-(4-Bromobenzyl)-1H-imidazol-5-yl]-1-propanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11.2 g of 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-1H-imidazole and 12.49 g of p-bromobenzyl bromide in 110 ml of acetonitrile is refluxed for 24 h. The solution is cooled to 0° and ammonia gas is bubbled through the reaction mixture for 5 min. After reacting an additional 45 min at room temperature, the solvent is evaporated. The residue is taken up in 100 ml of 1N hydrochloric acid and extracted with 50 ml of ether. The aqueous phase is adjusted to pH 8 and extracted with ethyl acetate (5×50 ml). The organic extracts are washed with water, dried over sodium sulfate and evaporated. The resulting oil is chromatographed on 530 g of silica gel with ethyl acetate:methanol:saturated NH4OH (90:5:5) to yield the title compound (a) as an oil; NMR: δ 5.00 (s, 2H).

Workup

  1. temperatureThe solution is cooled to 0°
  2. customammonia gas is bubbled through the reaction mixture for 5 min
  3. customthe solvent is evaporated
  4. extractionextracted with 50 ml of ether
  5. extractionextracted with ethyl acetate (5×50 ml)
  6. washThe organic extracts are washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe resulting oil is chromatographed on 530 g of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-b8ada113ef3d418f992d13ba9ef17110
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Linked notes

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