Iodoethane → HCID 12750810, compound

HRID 866491Notes

Reaction equation

HRID 866491 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=3)[CH:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:7][C:6]2=[O:22])[CH2:3][CH2:2]1.[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=3)[CH:8]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:7]([CH2:25][CH3:26])[C:6]2=[O:22])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12234598HCID 12234598, compound

Product 1

HCID 12750810HCID 12750810, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.1 g. of 1-cyclopropylmethyl-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone in 50 ml. of dimethylformamide was added 0.42 g. of 63% sodium hydride, and the resulting mixture was stirred at 50° C. for 30 minutes. Thereafter, 3.1 g. of ethyl iodide was added, and the mixture was stirred at 60° C. for 4 hours. After cooling, the reaction mixture was poured into 300 ml. of water and extracted with chloroform, and the chloroform layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was adsorbed on a silica gel column, eluted with chloroform to obtain yellow oily 1-cyclopropylmethyl-3ethyl-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone. Crystallization from petroleum benzine gave colorless prisms having a melting point of 88°-90° C.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into 300 ml
  3. extractionof water and extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-40acf3ba915041b09667e5659b40f7a5
Source dataset
uspto-grants-1978_07
Patent number
US04099002

Reaction notes

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