Water → HCID 14458977, compound

HRID 1639314Notes

Reaction equation

HRID 1639314 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7](=[O:19])[NH:6][C:5]2=[O:20].[H-].[Na+].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[C:26]([F:32])[CH:25]=1.O>CN(C)C=O>[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:6]2[C:5](=[O:20])[C:4]3[C:9](=[CH:10][C:11]([Cl:12])=[C:2]([Cl:1])[CH:3]=3)[N:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]2=[O:19])=[C:26]([F:32])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 14459011HCID 14459011, compound

Product 1

HCID 14458977HCID 14458977, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl 2-(6,7-dichloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl)acetate (2.0 g) in N,N-dimethylformamide (50 ml) was added sodium hydride (60% in mineral oil, 288 mg) at room temperature with stirring and the mixture was stirred at the same temperature for 1 hour. To this mixture was added 4-bromo-2-fluorobenzyl bromide (1.93 g) at room temperature with stirring and the mixture was stirred at the same temperature for 2 hours. The solvent was removed to give a residue, which was poured into water. The resulting precipitates were collected by filtration and washed with n-hexane to give ethyl 2-[3-(4-bromo-2-fluorobenzyl)-6,7-dichloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (2.94 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringwith stirring
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. customThe solvent was removed
  5. customto give a residue, which
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-d014e4536d264497b9d63035179a6e24
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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