Diethylaminoethyl chloride → HCID 20321463, compound

HRID 866492Notes

Reaction equation

HRID 866492 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=3)[CH:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:7][C:6]2=[O:22])[CH2:3][CH2:2]1.[H-].[Na+].[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29]Cl)[CH3:26].O.N>O.CN(C)C=O>[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=3)[CH:8]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:7]([CH2:26][CH2:25][N:27]([CH2:31][CH3:32])[CH2:28][CH3:29])[C:6]2=[O:22])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydrideHCID 12234598HCID 12234598, compoundHCID 12896473Azane;hydrate

Product 1

HCID 20321463HCID 20321463, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3.1 g. of 1-cyclopropylmethyl-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone in 50 ml. of dimethylformamide was added 0.42 g. of 63% sodium hydride, and the resulting mixture was stirred at 50° C. for 30 minutes. Thereafter, 2.7 g. of β-diethylaminoethyl chloride was added, and the mixture was stirred at 100° C. for 8 hours. After cooling, the reaction mixture was poured into 300 ml. of water, and ammonia water was added thereto to make alkaline. The resulting mixture was extracted with benzene. The benzene layer was washed with water and dried, and then the solvent was removed under reduced pressure. The residue was dissolved in 50 ml. of ether, and the insoluble material were separated by filtration. The filtrate was extracted with 50 ml. of 5% hydrochloric acid, and the water layer was further washed with ether, made alkaline by addition of ammonia water and then extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was removed to obtain oily 1-cyclopropylmethyl-3-(β-diethylaminoethyl)-3,4-dihydro-4-phenyl-6-chloro-2(1H)-quinazolinone.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into 300 ml
  3. extractionThe resulting mixture was extracted with benzene
  4. washThe benzene layer was washed with water
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in 50 ml
  8. customof ether, and the insoluble material were separated by filtration
  9. extractionThe filtrate was extracted with 50 ml
  10. washof 5% hydrochloric acid, and the water layer was further washed with ether
  11. additionby addition of ammonia water
  12. extractionextracted with ether
  13. washThe ether layer was washed with water
  14. dry with materialdried over anhydrous sodium sulfate
  15. customthe solvent was removed

Sources & evidence

ORD record
ord-fc2f9e0b75444b08b0bb23c59896f646
Source dataset
uspto-grants-1978_07
Patent number
US04099002

Reaction notes

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