Sodium Hydroxide → HCID 57104926, compound

HRID 1076361Notes

Reaction equation

HRID 1076361 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[C:8]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[OH-].[Na+]>O1CCCC1>[N:1]1([C:8]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 2141232159870-44-9

Product 1

HCID 57104926HCID 57104926, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.4 g of pyrrolidine in 50 ml of tetrahydrofuran was added to 10 g of 2-chloro-4-(2-diethylaminoethylamino)quinazoline hydrochloride in 100 ml of tetrahydrofuran. The reaction mixture was stirred at ambient temperature for about one hour and then was heated at reflux for 5 hours. The reaction mixture was poured into ice-water, made alkaline by the addition of dilute aqueous sodium hydroxide solution, and extracted with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated. The residue, a gummy solid, was triturated with about 5 ml of hexane, and the resulting mixture was chilled overnight in a refrigerator. The mixture then was filtered and the solid obtained was recrystallized from aqueous ethanol to give 2 g of 2-pyrrolidinyl-4-(2-diethylaminoethylamino)quinazoline; m.p. 87°-90°. The following analytical data were obtained:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, a gummy solid, was triturated with about 5 ml of hexane
  10. temperaturethe resulting mixture was chilled overnight in a refrigerator
  11. filtrationThe mixture then was filtered
  12. customthe solid obtained
  13. customwas recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-ba0f365538f641fa8ef00cb0c7188eca
Source dataset
uspto-grants-1976_05
Patent number
US03956495

Reaction notes

Loading…