Dipropylamine → HCID 13343516, compound

HRID 637704Notes

Reaction equation

HRID 637704 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[CH3:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19]Br)=[CH:17][C:12]=2[O:11][C:10]1=[O:21]>O1CCOCC1>[CH3:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[CH:17][C:12]=2[O:11][C:10]1=[O:21]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 13306088HCID 13306088, compound

Product 1

HCID 13343516HCID 13343516, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.02 g (0.02 mol) of N,N-dipropylamine and 2.56 g (0.01 mol) of 3-methyl-6-(2-bromoethyl)-benzoxazolinone, dissolved beforehand in 30 cm3 of dioxane, were introduced into a 100 cm3 flask with a ground glass neck, fitted with a reflux condenser, and the mixture was then heated under reflux for seventy-two hours, with stirring. After cooling, the reaction mixture was filtered and the filtrate was then evaporated in a water-bath, in vacuo. The residue was then taken up in 30 cm3 of diethylether, the solution was filtered, the filtrate was washed with water and dried over calcium chloride, and a stream of hydrogen chloride was then bubbled. The precipitate formed was filtered off and then recrystallised from ethylacetate, and this gave 2.23 g of the title compound, in the form of the hydrochloride, having a melting point of 150°-152° C.

Workup

  1. additionwere introduced into a 100 cm3 flask with a ground glass neck
  2. customfitted with a reflux condenser
  3. temperaturethe mixture was then heated
  4. temperatureunder reflux for seventy-two hours
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. customthe filtrate was then evaporated in a water-bath, in vacuo
  8. filtrationthe solution was filtered
  9. washthe filtrate was washed with water
  10. dry with materialdried over calcium chloride
  11. customa stream of hydrogen chloride was then bubbled
  12. customThe precipitate formed
  13. filtrationwas filtered off
  14. customrecrystallised from ethylacetate

Sources & evidence

ORD record
ord-89a00e9b52f64ef49edd7756475c9bd5
Source dataset
uspto-grants-1985_12
Patent number
US04558060

Reaction notes

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