Iodoethane → HCID 67263631, compound

HRID 1040755Notes

Reaction equation

HRID 1040755 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]2[CH:11]3[CH2:15][CH2:16][N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:23](I)[CH3:24]>CC(C)=O>[CH2:16]([N:7]1[CH2:6][CH:12]2[CH2:11][CH2:10][CH:9]([C:23]3[CH:24]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][C:13]=32)[CH2:8]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67264332HCID 67264332, compound

Product 1

HCID 67263631HCID 67263631, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Nitro-1-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene (82 mg, 0.376 mmol) was dissolved in acetone (5 mL) and K2CO3 (104 mg, 0.752 mmol, 2.0 eq) and ethyl iodide (64.2 mg, 0.414 mmol, 32.9 μL, 1.1 eq) were added. The reaction was stirred at room temperature for 48 hours. The reaction was then concentrated under reduced pressure and the residue was taken up in CH2Cl2 (10 mL) and washed with water (10 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-20% MeOH/CH2Cl2 as the eluting solvent to obtain 10-ethyl-4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene as a pale orange oil (68 mg, 73%). LCMS (m/e) 247 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.03 (dd, 1H, J=2.3 and 8.1 Hz), 7.94 (d, 1H, J=2.3 Hz), 7.20 (d, 1H, J=8.1 Hz), 3.17-3.08 (m, 2H), 2.95-2.86 (m, 2H), 2.43 (q, 2H, J=7.1 Hz), 2.30-2.19 (m, 4H), 1.66-1.57 (m, 2H), 0.99 (t, 3H, J=7.1 Hz).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. washwashed with water (10 mL)
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2c050258061445d1b62e194d59645905
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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