Sodium Hydroxide → HCID 57104926, compound

HRID 2071760Notes

Reaction equation

HRID 2071760 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 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 for 5 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue, a gummy solid, was triturated with about 5 ml of hexane
  9. temperaturethe resulting mixture was chilled overnight in a refrigerator
  10. filtrationThe mixture then was filtered
  11. customthe solid obtained
  12. customwas recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-b4cfbc9f5ab34142ae6448866d7c64e5
Source dataset
uspto-grants-1977_09
Patent number
US04048312

Reaction notes

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