Cyclohexane → HCID 58204579, compound

HRID 1629081Notes

Reaction equation

HRID 1629081 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][O:7][C:6]=2[CH:13]=1.C1CCCCC1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])/[C:10](=[CH:22]/[N:23]([CH3:25])[CH3:24])/[CH2:9][CH2:8][O:7][C:6]=2[CH:13]=1

Participants

4

Reactant 3

HCID 8078CyclohexaneHCID 78373Dimethylformamide dimethyl acetalHCID 103770258-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 58204579HCID 58204579, compoundYield 86%

Procedure

8-Bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (5.0 g, 20.7 mmol) in dimethylformamide dimethylacetal (15 mL) was heated at 110° C. for 18 h. The reaction was allowed to cool to room temperature and cyclohexane (20 mL) was added. The resulting solid precipitate was collected by filtration, washed with cyclohexane and then dried under vacuum at 40° C. to yield 8-Bromo-4-[1-dimethylamino-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]-oxepin-5-one as yellow crystals (5.32 g, 86%). 1H NMR δ (ppm)(CDCl3): 7.73 (1 H, s), 7.61 (1 H, d, J=8.29 Hz), 7.29 (1 H, dd, J=8.29, 1.94 Hz), 7.18 (1 H, d, J=1.91 Hz), 4.28-4.21 (2 H, m), 3.14 (6 H, s), 2.77-2.70 (2 H, m).

Workup

  1. filtrationThe resulting solid precipitate was collected by filtration
  2. washwashed with cyclohexane
  3. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-70ed361ee5124e6daaac4a6694608bb9
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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