Lithium hydride → HCID 20339576, compound

HRID 1395527Notes

Reaction equation

HRID 1395527 reaction equation
[H-].[Li+].[CH3:3][N:4]([CH3:16])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)=[O:6].[ClH:17].[CH:18]([N:21]([CH:25]([CH3:27])[CH3:26])[CH2:22][CH2:23][Cl:24])([CH3:20])[CH3:19]>O1CCOCC1>[ClH:24].[ClH:17].[CH3:3][N:4]([CH3:16])[C:5]([N:7]([CH2:23][CH2:22][N:21]([CH:25]([CH3:27])[CH3:26])[CH:18]([CH3:20])[CH3:19])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 12857657HCID 12857657, compound

Product 1

HCID 20339576HCID 20339576, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of lithium hydride (0.65 g, 80 mmoles) in dry dioxane (65 ml) under nitrogen atmosphere is added N,N-dimethyl-N'-(4,6-dimethyl-2-pyridyl)urea (5.8 g, 30 mmoles) and the mixture is heated to reflux for three hours. 2-Diisopropylaminoethyl chloride hydrochloride (6.0 g, 30 mmoles) is added cautiously in small portions and refluxing continued for twenty-four hours. The reaction mixture is cooled, salts filtered off and solvent evaporated. The residue is dissolved in methylene chloride and the product is extracted into dilute aqueous hydrochloric acid (10%). This solution is filtered through charcoal, made basic with saturated sodium carbonate, and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate, filtered and evaporated. The crude product (8.3 g) is taken up in diethyl ether, insoluble material is removed by filtration and hydrogen chloride gas is bubbled into the filtrate. The precipitated salt is collected and recrystallized from isopropanol to give 5.2 g (44.0% yield) of product, m.p. 182°-186° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for three hours
  3. temperaturerefluxing
  4. waitcontinued for twenty-four hours
  5. temperatureThe reaction mixture is cooled
  6. filtrationsalts filtered off
  7. customsolvent evaporated
  8. dissolutionThe residue is dissolved in methylene chloride
  9. extractionthe product is extracted into dilute aqueous hydrochloric acid (10%)
  10. filtrationThis solution is filtered through charcoal
  11. extractionextracted with methylene chloride
  12. dry with materialThe extract is dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. custominsoluble material is removed by filtration and hydrogen chloride gas
  16. customis bubbled into the filtrate
  17. customThe precipitated salt is collected
  18. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-acd2410ab7f347669f59fae084540bb5
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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