Iodoethane → HCID 19910559, compound

HRID 1534092Notes

Reaction equation

HRID 1534092 reaction equation
[Cl:1][C:2](=[CH2:20])[CH2:3][N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[NH:7][C:6]2[N:16]=[CH:17][CH:18]=[CH:19][C:5]1=2.[H-].[Na+].[CH2:23](I)[CH3:24]>CN(C)C=O>[Cl:1][C:2](=[CH2:20])[CH2:3][N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[N:7]([CH2:23][CH3:24])[C:6]2[N:16]=[CH:17][CH:18]=[CH:19][C:5]1=2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19910552HCID 19910552, compound

Product 1

HCID 19910559HCID 19910559, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.7 g (0.034 mol) of 5-(2-chloro-2-propenyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, were suspended in 100 ml of anhydrous dimethylformamide. The mixture was thoroughly purged with dry nitrogen and stirred rapidly while 1.8 g (0.0375 mol) of a 50% dispersion of sodium hydride in mineral oil was slowly added portionwise through an inlet protected by a calcium chloride drying tube. Addition of the first portion sodium hydride resulted in an immediate exothermic reaction, and the temperature of the mixture rose rapidly to about 60° C. After addition of the sodium hydride was complete (30-35 minutes), the reaction mixture was cooled to room temperature, and 7.8 g (0.05 mol) of ethyl iodide were added dropwise. Thereafter, the flask was placed in an oil bath heated to 100° C., and the reaction mixture was stirred and heated for 2 hours, during which time a slow stream of dry nitrogen was passed through the apparatus. After this time no starting material was detected by thin-layer chromatography.

Workup

  1. customThe mixture was thoroughly purged with dry nitrogen
  2. additionwas slowly added portionwise through an inlet
  3. customprotected by a calcium chloride drying tube
  4. additionAddition of the first portion sodium hydride
  5. customresulted in an immediate exothermic reaction
  6. customrose rapidly to about 60° C
  7. custom(30-35 minutes)
  8. customThereafter, the flask was placed in an oil bath
  9. temperatureheated to 100° C.
  10. stirringthe reaction mixture was stirred
  11. temperatureheated for 2 hours, during which time a slow stream of dry nitrogen

Sources & evidence

ORD record
ord-e368998b55434ee999530db01c5d5268
Source dataset
uspto-grants-1992_02
Patent number
US05087625

Reaction notes

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