2-Bromo-6-phenylcyclohexanone → HCID 44193962, compound

HRID 2076139Notes

Reaction equation

HRID 2076139 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.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>[CH3:1][C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][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:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632616HCID 86632616, compound

Product 1

HCID 44193962HCID 44193962, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(2,4-dimethyl-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 precipitated solid was filtered off after cooling to room temperature and dried to yield the title compound (170 mg, 85%) as a light brown solid. MS ISP (m/e): 402.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.37 (br s, 1H, NH), 7.53 (d, 2H), 7.42 (d, 2H), 7.30 (t, 2H), 7.20 (t, 1H), 7.12 (d, 1H), 4.05 (m, 1H), 2.72 (m, 2H), 2.39 (s, 3H), 2.24 (s, 3H), 2.12 (m, 1H), 1.70-1.88 (m, 3H).

Workup

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-3b1998ab4c074e60a84c726ed700dccd
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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