2-Bromo-6-phenylcyclohexanone → [4-(4-Methyl-imidazol-1-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076007Notes

Reaction equation

HRID 2076007 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)[CH:6]=1.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=O>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[S:15][C:26]4[CH2:27][CH2:28][CH2:29][CH:24]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=5)[C:25]=4[N:16]=3)=[CH:11][CH:12]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86624711[4-(4-Methyl-imidazol-1-yl)-phenyl]-thiourea

Product 1

HCID 44195184[4-(4-Methyl-imidazol-1-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (29.2 mg, 0.13 mmol) and of 2-bromo-6-phenyl-cyclohexanone (65.5 mg, 0.26 mmol) in ethanol (2 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 using dichloromethane then dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (50 mg, 100%) as an colourless oil. MS ISP (m/e): 387.4 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.12 (s, 1H), 7.95 (s, 1H), 7.52 (d, 2H), 7.39 (d, 2H), 7.29 (m, 3H), 7.11-7.20 (m, 3H), 4.02 (m, 1H), 2.71 (m, 2H), 2.13 (s, 3H), 2.12 (m, 1H), 1.70-1.94 (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

Sources & evidence

ORD record
ord-cdd5122738164e9bba5926289d5d1c2c
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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