2-Bromo-6-phenylcyclohexanone → HCID 86632611, compound

HRID 2076124Notes

Reaction equation

HRID 2076124 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][C:3]=1[O:12][CH3:13].Br[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]1=O>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:23]3[CH2:24][CH2:25][CH2:26][CH:21]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:15][CH:16]=4)[C:22]=3[N:11]=2)=[CH:4][C:3]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 58110048HCID 58110048, compound

Product 1

HCID 86632611HCID 86632611, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Bromo-3-methoxy-phenyl)-thiourea (1.20 g, 4.59 mmol) and 2-bromo-6-phenyl-cyclohexanone (1.29 g, 5.10 mmol) in 20 ml ethanol were stirred overnight at reflux. The brown solution was evaporated to dryness; the brown residue was dissolved in chloroform, washed three times with water and dried with magnesium sulfate. The solvent was evaporated in vacuo. Column chromatography (70 g silica, dichloromethane) afforded the title compound (1.18 g, 62%) as a light brown foam. MS ISP (m/e): 417.1 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): □ (ppm)=7.25 (m, 7H), 6.90 (s broad, 1H), 6.50 (dd, 1H), 4.04 (m broad, 1H), 3.58 (s, 3H), 2.75 (m broad, 2H), 2.20 (m broad, 1H), 1.77 (m broad, 3H).

Workup

  1. temperatureat reflux
  2. customThe brown solution was evaporated to dryness
  3. dissolutionthe brown residue was dissolved in chloroform
  4. washwashed three times with water
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4942618f2b14457f887646e0e1bd7fac
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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