Water → 2-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-1-(phenylmethyl)-1H-imidazole

HRID 1447027Notes

Reaction equation

HRID 1447027 reaction equation
[H-].[Na+].[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[CH2:19]([N:18]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:13][CH:4]1[O:3][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 127617562-(1,4-BENXODIOXAN-2YL)-METHYLENE-IMIDAZOLE

Product 1

HCID 127617712-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-1-(phenylmethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.0 g of 50% dispersion in oil) was added to a solution of 2-(1,4-benzodioxan-2-ylmethyl)-imidazole (5.2 g) in dimethylformamide (50 ml) and the resulting mixture was stirred for 30 minutes. The solution was cooled in an ice bath and benzyl bromide (3 ml) was added. After warming to room temperature the mixture was poured into water (250 ml) and extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts were combined, washed with water (3×100 ml), dried over sodium sulfate, and evaporated. The residue was dissolved in methanolic hydrochloric acid and ether was added until an oil came out of solution. The oil was crystallized from isopropanol-ether to give the title compound (2.10 g) as a white powder, m.p. 105°-107° C.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washwashed with water (3×100 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in methanolic hydrochloric acid
  7. additionether was added until an oil
  8. customThe oil was crystallized from isopropanol-ether

Sources & evidence

ORD record
ord-b6c35d9a7c994870b9581c812edd5855
Source dataset
uspto-grants-1982_02
Patent number
US04315021

Reaction notes

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