Iodoethane → HCID 9834404, compound

HRID 1040656Notes

Reaction equation

HRID 1040656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:14]=1.[H-].[Na+].I[CH2:18][CH3:19]>CN(C)C=O>[CH2:18]([N:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]1=2)[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Product 1

HCID 9834404HCID 9834404, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.10 g, 0.00575 mol) was charged into RBF fit with stir bar, septum and under N2 atmosphere. Charged with N,N-Dimethylformamide (25 mL) and then Sodium Hydride (60% dispersion mineral oil) (0.25 g), gas evolution (H2) ensued. The mixture was stirred about 5 minutes and then treated with Iodoethane (0.63 mL, 0.0078 mol) and stirred at room temperature for 1.3 h. The mixture was quenched with ice/water and extracted with ether. The ether layer was washed with water, then with brine, dried (MgSO4), filtered and concentrated to give a 1-Ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as a clear oil (1.19 g, 94%). 1H-NMR (CDCl3) δ 7.21 (t, J=8.2 Hz, 1H), 6.83 (d, J=8.1 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 3.84 (s, 3H), 2.25 (s, 2H), 1.7-3.5 (br pk's, 6H), 1.13 (t, J=7.2 Hz, 3H); LC/MS (ESI-pos) m/z 220.09 (M+H). M.P.=Oil. LC/MS: 220.06 (M+H).

Workup

  1. stirringThe mixture was stirred about 5 minutes
  2. stirringstirred at room temperature for 1.3 h
  3. customThe mixture was quenched with ice/water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialwith brine, dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-40487af279414e46a216150fcc3d7182
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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