Imidazole → HCID 22009688, compound

HRID 322255Notes

Reaction equation

HRID 322255 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)(=O)=O.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:10][CH:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13079701HCID 13079701, compound

Product 1

HCID 22009688HCID 22009688, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-benzyloxyphenyl)propyl methanesulfonate (55.0 g), imidazole (17.6 g), potassium carbonate (35.7 g) and N,N-dimethylformamide (500 ml) was stirred for 6 hours at 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 1-[3-(4-benzyloxyphenyl)propyl]imidazole (34.7 g, 69%). Recrystallization from ethyl acetate-hexane gave colorless needles, mp 80-81° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20290697e30d452ebd4ab938c9791c1c
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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