1-Bromopentane → HCID 15675476, compound

HRID 974017Notes

Reaction equation

HRID 974017 reaction equation
[CH2:1]([O:8][N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH2:1]([O:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:10]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 15675475HCID 15675475, compound

Product 1

HCID 15675476HCID 15675476, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of this imidazolidinone (4.0 g, 20.8 mmol) in DMF (50 ml) under nitrogen at 50° C. was added sodium hydride (1.0 g of a 60% dispersion in oil). A thick slurry formed at once. After 30 minutes, 1-bromopentane (2.84 ml) was added. After 15 minutes, the resulting clear solution was evaporated, and the residue was partitioned between ether and water. The organic extract was washed with water and brine, then dried (MgSO4), filtered, and evaporated. Purification by chromatography on silica provided 3-benzyloxy-1-pentyl-2-imidazolidinone as a colorless oil (4.15 g, 83% yield). Hydrogenolysis as in Example 2 above provided the title compound, after purification by chromatography on silica, as a white solid, mp 60°-61° C.

Workup

  1. customA thick slurry formed at once
  2. waitAfter 15 minutes
  3. customthe resulting clear solution was evaporated
  4. customthe residue was partitioned between ether and water
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-f86c56a219014504a750f43cb813318e
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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