Potassium Carbonate → HCID 178516699, compound

HRID 2166882Notes

Reaction equation

HRID 2166882 reaction equation
Br.[NH2:2][C:3]1[N:12](CC2C=CC(OC)=CC=2)[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:22])[N:4]=1.I[CH2:24][C:25](OCC)=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:22][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][NH:12][C:3]1[N:4]2[CH2:24][C:25](=[O:26])[N:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 20497179HCID 20497179, compound

Product 1

HCID 178516699HCID 178516699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.15 mol of 2-amino-5-chloro-3,4-dihydro-3-(p-methoxybenzyl)-quinazoline hydrobromide in 800 ml of dimethylformamide is treated with 0.18 mol of ethyl iodoacetate and 0.2 mol of potassium carbonate and stirred at room temperature for 18 hours. Then, the mixture is stirred at 90° for an additional 5 hours, cooled and poured into 5 l of ice/water. The precipitated product, 6-chloro-4-(p-methoxybenzyl)-5H-imidazo[1,2-a]quinazolin-2(1H)-one, is removed by filtration and washed well with water. In order to prepare the hydrochloride, the product is recrystallized from ethanol/hydrochloric acid; m.p. 230° (decomposition).

Workup

  1. stirringThen, the mixture is stirred at 90° for an additional 5 hours
  2. temperaturecooled
  3. customThe precipitated product, 6-chloro-4-(p-methoxybenzyl)-5H-imidazo[1,2-a]quinazolin-2(1H)-one, is removed by filtration
  4. washwashed well with water
  5. customIn order to prepare the hydrochloride
  6. customthe product is recrystallized from ethanol/hydrochloric acid

Sources & evidence

ORD record
ord-49189b62c91242c09ed9559274f4742d
Source dataset
uspto-grants-1983_06
Patent number
US04390540

Reaction notes

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