Hydrochloric Acid → HCID 22449628, compound

HRID 2187060Notes

Reaction equation

HRID 2187060 reaction equation
[H-].[Na+].[O:3]=[C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:12](=[O:23])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.Cl>CN(C)C=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:23])[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C:4]1=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 15923531HCID 15923531, compound

Product 1

HCID 22449628HCID 22449628, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 4.34 g) in N,N-dimethylformamide (100 ml), 2,4-dioxo-3-(4-methoxybenzyl)-1,2,3,4-tetrahydroquinazoline (25.5 g) obtained in Reference Example 26 was added, and the mixture was stirred at room temperature for 2 hours. This mixture was treated dropwise with a solution of 1,4-dibromobutane (21.6 ml) in N,N-dimethylformamide (50 ml), and stirred at room temperature for 19 hours. The reaction mixture was admixed with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), and the solvent was distilled off under reduced pressure to give the title compound (30.8 g, 82%). Recrystallization from ethyl acetate-ethyl ether yielded a colorless crystal having a melting point of 124 to 125° C.

Workup

  1. customobtained in Reference Example 26
  2. additionwas added
  3. stirringstirred at room temperature for 19 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1dcd69f5fd5b4fd493590c1b33312861
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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