2-Chloro-N,N-dimethylethylamine → HCID 57312351, compound

HRID 2295036Notes

Reaction equation

HRID 2295036 reaction equation
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C=NN2[CH2:27][CH2:26][N:25]([CH2:28]CCCI)[C:24]2=O)C=CC=CC=1.[H-].[Na+].CN(CCCl)C>CN(C)C=O.O>[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:27][CH2:26][N:25]([CH3:28])[CH3:24])[C:10]2=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 19261677HCID 19261677, compoundHCID 57037835HCID 57037835, compound

Product 1

HCID 57312351HCID 57312351, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-phenylmethyleneamino-2-imidazolidinone (prepared as described in Part II of Example A (14.4 g, 0.076 mole) in dry dimethylformamide (338 ml) is stirred and treated portionwise over a 3 minute period with sodium hydride (60% dispersion in mineral oil) (3.0 g, 0.023 mole). During the addition, a nitrogen sweep is maintained. After the addition is complete, the reaction is heated on a steam bath for 15 minutes and then chilled to ambient temperature. The nitrogen sweep is discontinued and the reaction mixture is treated all at once with dimethylaminoethyl chloride (17.66 g, 0.16 mole), prepared as described in Part I herein. The reaction is stirred at ambient temperature for 15 minutes and then heated at 80° to 90° C. for 3 hours. The reaction is filtered hot, and the filtrate is chilled and concentrated under reduced pressure to leave an oily residue. The residue is treated with 300 ml of water and extracted with 3×300 ml portions of chloroform. The extracts are combined and dried over anhydrous MgSO4. The extract is filtered and the filtrate is concentrated under reduced pressure to leave a tan-colored semi-solid. The semi-solid is triturated with anhydrous ether to give the 1-phenylmethyleneamino-3-[2-(dimethylamino)ethyl]-2-imidazolidinone, weighing 6.17 g.

Workup

  1. additionDuring the addition
  2. temperaturea nitrogen sweep is maintained
  3. additionAfter the addition
  4. temperaturethe reaction is heated on a steam bath for 15 minutes
  5. customprepared
  6. stirringThe reaction is stirred at ambient temperature for 15 minutes
  7. temperatureheated at 80° to 90° C. for 3 hours
  8. filtrationThe reaction is filtered hot
  9. temperaturethe filtrate is chilled
  10. concentrationconcentrated under reduced pressure
  11. customto leave an oily residue
  12. extractionextracted with 3×300 ml portions of chloroform
  13. dry with materialdried over anhydrous MgSO4
  14. filtrationThe extract is filtered
  15. concentrationthe filtrate is concentrated under reduced pressure
  16. customto leave a tan-colored semi-solid
  17. customThe semi-solid is triturated with anhydrous ether

Sources & evidence

ORD record
ord-e6533e45f83a498d92a528ee980ffdaa
Source dataset
uspto-grants-1997_11
Patent number
US05691369

Reaction notes

Loading…