Cyclohexane → HCID 58204454, compound

HRID 1498111Notes

Reaction equation

HRID 1498111 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C1CCCCC1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH2:8]/[C:9](=[CH:22]\[N:23]([CH3:25])[CH3:24])/[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 8078CyclohexaneHCID 78373Dimethylformamide dimethyl acetalHCID 106815487-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

Product 1

HCID 58204454HCID 58204454, compoundYield 67%

Procedure

7-Bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (10.0 g, 41.5 mmol) in dimethylformamide dimethylacetal (100 mL) was heated at 110° C. for 18 h. The reaction was allowed to cool to room temperature and cyclohexane (100 mL) was added. The resulting solid precipitate was collected by filtration, washed with cyclohexane and then dried under vacuum at 40° C. to yield 7-Bromo-4-[1-dimethylamino-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]-oxepin-5-one as yellow crystals (8.19 g, 67%). 1H NMR δ (ppm) (CDCl3): 7.83 (1 H, d, J=2.59 Hz), 7.74 (1 H, s), 7.46 (1 H, dd, J=8.51, 2.58 Hz), 6.88 (1 H, d, J=8.52 Hz), 4.27-4.19 (2 H, m), 3.14 (6 H, s), 2.76-2.69 (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-6e8d05f7f3f849e6bec5a5a3f6d70f06
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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