Iodoethane → HCID 20321457, compound

HRID 866490Notes

Reaction equation

HRID 866490 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][N:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:22])[CH:13]=2)[NH:8][C:7]1=[O:23])[CH3:2].[H-].[Na+].[CH2:28]([I:30])[CH3:29]>CN(C)C=O>[IH:30].[CH2:28]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:6]([CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])[C:7]1=[O:23])[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12750777HCID 12750777, compound

Product 1

HCID 20321457HCID 20321457, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.07 g. of 3-(β-diethylaminoethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone in 20 ml. of dimethylformamide was added 0.13 g. of 64% sodium hydride, and the resulting mixture was heated with stirring at 60° C (bath temperature) for 1 hour. Thereafter, 0.94 g. of ethyl iodide was added thereto at room temperature, and the mixture was stirred at 100° C (bath temperature) for 4 hours. After cooling, the reaction mixture was poured into 100 ml. of water, extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure to obtain colorless oily 1-ethyl-3-(β-diethylaminoethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone hydroiodide. This compound was crystallized from ethanol-petroleum benzine to give colorless fine crystals having a melting point of 198°-199° C (decomp.).

Workup

  1. stirringat room temperature, and the mixture was stirred at 100° C (bath temperature) for 4 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured into 100 ml
  4. extractionof water, extracted with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8fb05c258a194378bdb587a715470e30
Source dataset
uspto-grants-1978_07
Patent number
US04099002

Reaction notes

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