1-Chloro-4-(chloromethyl)benzene → HCID 14423765, compound

HRID 1639308Notes

Reaction equation

HRID 1639308 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:13]2[C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:4]2=[O:3])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 10198809HCID 10198809, compound

Product 1

HCID 14423765HCID 14423765, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 367 mg) in N,N-dimethylformamide (15 ml) was added a solution of ethyl 2-(1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl)acetate (2.0 g) in N,N-dimethylformamide (35 ml) with stirring at room temperature under nitrogen atmosphere, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added 4-chlorobenzyl chloride (1.48 g) with stirring at room temperature and the mixture was stirred at the same temperature for 1 hour. The solvent was evaporated in vacuo to give a residue, which was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and dried. Evaporation of the solvent gave a residue, which was washed with n-hexane to afford ethyl 2-[3-(4-chlorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (2.55 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 minutes
  2. stirringwith stirring at room temperature
  3. stirringthe mixture was stirred at the same temperature for 1 hour
  4. customThe solvent was evaporated in vacuo
  5. customto give a residue, which
  6. washThe ethyl acetate solution was washed with water
  7. customdried
  8. customEvaporation of the solvent
  9. customgave a residue, which
  10. washwas washed with n-hexane

Sources & evidence

ORD record
ord-f8346277088444c1964fb59bebac03e5
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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