Diethylamine → HCID 13769161, compound

HRID 2232534Notes

Reaction equation

HRID 2232534 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][CH:14]([CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:20]=1)[C:15](O)=[O:16].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>O1CCCC1>[CH2:35]([N:37]([CH2:38][CH3:39])[C:15](=[O:16])[CH:14]([CH3:13])[CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:20]=1)[CH3:36]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 9811219HCID 9811219, compound

Product 1

HCID 13769161HCID 13769161, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (1.65 g) is added to a stirred solution of dextrorotatory α-methyl-2-phenyl-4-quinazolinepropanoic acid (2 g) in tetrahydrofuran (20 cc). The mixture is stirred for about 20 minutes until the evolution of gas has ceased, and then for a further hour, and diethylamine (1.05 cc) is added. The mixture is stirred for 5 days at room temperature (approximately 20° C.) and then heated under reflux for two hours. The solvent is evaporated off under reduced pressure and the residue taken up with ethyl ether (100 cc). The organic phase is washed with water (2×10 cc), then with normal hydrochloric acid solution (2×5 cc), then with normal sodium hydroxide solution (2×5 cc) and finally with water (2×5 cc). It is then dried over magnesium sulphate and evaporated under reduced pressure. The residue is recrystallized twice in isopropyl ether. Laevorotatory N,N-diethyl-α-methyl-2phenyl-4-quinazolinepropanamide (1.1 g , m.p. 93.5° C., is thereby isolated; αD at 0.5% in EtOH at 23° C.=-17.9°±2°.

Workup

  1. waitfor a further hour
  2. stirringThe mixture is stirred for 5 days at room temperature (approximately 20° C.)
  3. temperatureheated
  4. temperatureunder reflux for two hours
  5. customThe solvent is evaporated off under reduced pressure
  6. washThe organic phase is washed with water (2×10 cc)
  7. dry with materialIt is then dried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue is recrystallized twice in isopropyl ether

Sources & evidence

ORD record
ord-a75bb069e5304582922b585b7a9bda66
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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