Dimethylformamide → N-Carbobenzyloxymethylimidazoline

HRID 2398624Notes

Reaction equation

HRID 2398624 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[CH:2]1.CN(C)C=O.Br[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O>[C:13]([CH2:12][N:3]1[CH2:4][CH2:5][N:1]=[CH:2]1)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 62576Benzyl bromoacetateHCID 681562-Imidazoline

Product 1

HCID 20369282N-Carbobenzyloxymethylimidazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 14.0 g. (0.2 mole) of imidazoline in 150 ml. of dry dimethylformamide is added dropwise with cooling 22.9 g. (0.1 mole) of benzyl bromoacetate. When the addition is complete, the reaction is warmed to 50°-60° C. for several hours, and is then cooled and diluted with water (250 ml.). The product is extracted with diethyl ether, and the extracts are combined and washed several times with a saturated brine solution. The ether phase is dried over sodium sulfate and concentrated to an oil, which is used in the next reaction without purification.

Workup

  1. temperaturewith cooling 22.9 g
  2. additionWhen the addition
  3. temperaturethe reaction is warmed to 50°-60° C. for several hours
  4. temperatureis then cooled
  5. extractionThe product is extracted with diethyl ether
  6. washwashed several times with a saturated brine solution
  7. dry with materialThe ether phase is dried over sodium sulfate
  8. concentrationconcentrated to an oil, which
  9. customis used in the next reaction without purification

Sources & evidence

ORD record
ord-647b0a2b2fa44820853b42f696fba653
Source dataset
uspto-grants-1977_05
Patent number
US04025506

Reaction notes

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