1-Bromo-3-chloropropane → HCID 15923532, compound

HRID 2187059Notes

Reaction equation

HRID 2187059 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[CH2:25][CH2:26][CH2:27][Cl:28]>CN(C)C=O>[Cl:28][CH2:27][CH2:26][CH2:25][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

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 15923531HCID 15923531, compound

Product 1

HCID 15923532HCID 15923532, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 0.34 g) in N,N-dimethylformamide (30 ml), 2,4-dioxo-3-(4-methoxybenzyl)-1,2,3,4-tetrahydroquinazoline (2.0 g) obtained in Reference Example 26 was added, and the mixture was stirred at room temperature for 30 minutes. To this mixture, 1-bromo-3-chloropropane (1.05 ml) was added and the mixture was stirred for further 13.5 hours. The solvent was distilled off under reduced pressure, and the residue was combined with iN hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried (Na2SO4), and the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluting with n-hexane-ethyl acetate (5:1, v/v) to give the title compound (1.58 g, 62%). Recrystallization from ethyl acetate-isopropyl 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. stirringthe mixture was stirred for further 13.5 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried (Na2SO4)
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a0981af96f0449159655a41e585afd77
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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