2-Bromo-6-phenylcyclohexanone → HCID 44193961, compound

HRID 2076137Notes

Reaction equation

HRID 2076137 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][CH:9]=2)=[CH:6][N:7]=1)[CH3:2].Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=O>C(O)C>[CH2:1]([C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[S:16][C:27]4[CH2:28][CH2:29][CH2:30][CH:25]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:19][CH:20]=5)[C:26]=4[N:17]=3)=[CH:12][CH:13]=2)=[CH:6][N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632615HCID 86632615, compound

Product 1

HCID 44193961HCID 44193961, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(2-ethyl-oxazol-5-yl)-phenyl]-thiourea (124 mg, 0.50 mmol) and 2-bromo-6-phenyl-cyclohexanone (139 mg, 0.55 mmol) in ethanol (5 ml) was heated to reflux over night. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as eluent to yield the title compound (170 mg, 85%) as a brown solid. MS ISP (m/e): 402.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.18 (br s, 1H, NH), 7.49 (s, 4H), 7.26-7.30 (m, 3H), 7.19 (t, 1H), 7.12 (d, 1H), 4.05 (m, 1H), 2.77 (q, 2H), 2.75 (m, 2H), 2.12 (m, 1H), 1.70-1.88 (m, 3H), 1.25 (t, 3H).

Workup

  1. temperatureto reflux over night
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-794b6c8ea6f044b09d8131b3def7767b
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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