Iodoethane → HCID 9857209, compound

HRID 1057362Notes

Reaction equation

HRID 1057362 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:9]=2[NH:8][C:7]1=[O:19])=[O:5])[CH3:2].[CH2:20](I)[CH3:21].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:9]=2[N:8]([CH2:20][CH3:21])[C:7]1=[O:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 9921451HCID 9921451, compound

Product 1

HCID 9857209HCID 9857209, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3(R,S)-ethoxycarbonyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (0.45 g, 1.71 mmol), ethyl iodide (0.41 mL, 5.1 mmol) and Cs2CO3 (1.672 g, 5.1 mmol) in acetonitrile (5 mL) was stirred at room temperature for 6 hrs. The reaction mixture was filtered and the solid was washed with acetonitrile. The combined filtrate and washer were evaporated under reduced pressure. The crude product was purified by flash chromatography on a short silica gel column using EtOAc/hexane (3:7) as an eluent. The title compound (0.241 g, 48%) was obtained as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with acetonitrile
  3. customThe combined filtrate and washer were evaporated under reduced pressure
  4. customThe crude product was purified by flash chromatography on a short silica gel column

Sources & evidence

ORD record
ord-06ac65f17d2040cc817da751699302ce
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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