Iodoethane → HCID 67264196, compound

HRID 1687180Notes

Reaction equation

HRID 1687180 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:3]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:25][CH3:26]>CN(C=O)C>[CH2:25]([N:5]1[C:6](=[O:9])[CH2:7][CH2:8][C:2]([CH3:17])([CH3:1])[C:3]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:4]1=2)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 578538385,5-Dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 67264196HCID 67264196, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined 5,5-Dimethyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (520 mg, 2.22 mmol), cesium carbonate (1.52 g, 4.7 mmol), iodoethane (355 uL, 4.44 mmol) and DMF (12 mL). Stirred at room temp. for 2.5 hours. Evaporated off solvent, added water and extracted into methylene chloride. Dried organic layer over sodium sulfate, filtered and concentrated under reduced pressure to yield a brown solid, 1-Ethyl-5,5-dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (553 mg, 95%). mp 67° C.; LCMS: m/z=263.08 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.31 (d, 1H, J=2.5 Hz), 8.17 (dd, 1H, J=8.7, 2.6 Hz), 7.38 (d, 1H, J=8.8 Hz), 3.89 (m, 2H), 2.31 (m, 2H), 2.12 (m, 2H), 1.42 (s, 6H), 1.33 (m, 3H).

Workup

  1. customEvaporated off solvent
  2. additionadded water
  3. extractionextracted into methylene chloride
  4. filtrationDried organic layer over sodium sulfate, filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10d5a7a62e6a46b79b8e62d706eecb4d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…