Cyclohexane → HCID 58204579, compound

HRID 1498112Notes

Reaction equation

HRID 1498112 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-adc22bc45a8c4dd88a542f23e9e7d6e0
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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