Hydrochloric Acid → HCID 54236367, compound

HRID 2254057Notes

Reaction equation

HRID 2254057 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[C:9](=[O:23])[N:8]([CH2:24][C:25]([OH:27])=[O:26])[C:7]2=[O:28].[CH2:29](Br)[CH2:30][OH:31].Cl>O.CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[C:9](=[O:23])[N:8]([CH2:24][C:25]([O:27][CH2:29][CH2:30][OH:31])=[O:26])[C:7]2=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 53845258HCID 53845258, compound

Product 1

HCID 54236367HCID 54236367, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Into 10 ml of dried dimethylformamide were suspended 60 mg of sodium hydride (60%), and, to this was added dropwise a solution dissolved 500 mg of 6-chloro-1-(2,4-dichlorophenyl)methyl-1,4-dihydro-2,4-dioxo-3-(2H)-quinazolineacetic acid into 3 ml of dried dimethylformamide under stirring. After stirring the mixture for 30 minutes at room temperature, 160 mg of ethylene bromohydrin were added and the mixture was stirred for 4 hours at 110° C. After cooling by allowing to stand, the reaction mixture was poured into 200 ml of water and acidified with hydrochloric acid, which was extracted with ethyl acetate. After dried over anhydrous magnesium sulfate, solvent was distilled off and the residue was recrystallized from ethanol to obtain 300 mg of title compound. m.p. 167°-168° C.

Workup

  1. additionto this was added dropwise a solution
  2. stirringAfter stirring the mixture for 30 minutes at room temperature
  3. stirringthe mixture was stirred for 4 hours at 110° C
  4. temperatureAfter cooling
  5. extractionwas extracted with ethyl acetate
  6. dry with materialAfter dried over anhydrous magnesium sulfate, solvent
  7. distillationwas distilled off
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-674612b1a8a740c8b335af3075eff5b1
Source dataset
uspto-grants-1993_08
Patent number
US05234928

Reaction notes

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