2-Bromo-6-phenylcyclohexanone → HCID 57400793, compound

HRID 2075995Notes

Reaction equation

HRID 2075995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]([NH2:17])=[S:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]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>[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]2[S:16][C:27]3[CH2:28][CH2:29][CH2:30][CH:25]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:19][CH:20]=4)[C:26]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86761297HCID 86761297, compound

Product 1

HCID 57400793HCID 57400793, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-chloro-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (66.7 mg, 0.25 mmol) and of 2-bromo-6-phenyl-cyclohexanone (63.3 mg, 0.25 mmol) in ethanol (4 mL) was stirred at room temperature for 30 minutes and then heated for two days to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified on silica gel with dichloromethane and then with dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (50 mg, 48%) as a pale-brown solid. MS ISP (m/e): 421.0/422.2 (100/38) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.38 (s, 1H), 8.31 (s, 1H), 7.82 (s, 1H), 7.60 (s, 1H), 7.46-7.10 (m, 7H), 6.98 (s, 1H), 4.03 (m, 1H), 2.72 (m, 2H), 2.13 (s, 3H), 2.11 (m, 1H), 1.70-1.90 (m, 3H).

Workup

  1. temperatureheated for two days
  2. temperatureto reflux under an atmosphere of nitrogen
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified on silica gel with dichloromethane

Sources & evidence

ORD record
ord-20c00536292d4eaf87ab3175f9599ce7
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

Loading…