Hydrochloric Acid → HCID 14423777, compound

HRID 1639307Notes

Reaction equation

HRID 1639307 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:17].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:7]1=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14458934HCID 14458934, compound

Product 1

HCID 14423777HCID 14423777, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazoline (1 g) in N,N-dimethylformamide (15 ml) was added sodium hydride (60% in mineral oil, 0.17 g) with stirring at 0° C. and the mixture was stirred for 15 minutes at the same temperature. To this mixture was added ethyl bromoacetate (0.45 ml) and the mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated to give a residue. Thus obtained product was purified by recrystallization from isopropyl ether to give ethyl 2-[3-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (1.21 g).

Workup

  1. stirringthe mixture was stirred for 15 minutes at the same temperature
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customdried
  6. customevaporated
  7. customto give a residue
  8. customThus obtained product was purified by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-7071d7ab2bb74c8a97b2e1c0a62efe77
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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