2-Bromo-6-phenylcyclohexanone → (3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2075974

Reaction equation

HRID 2075974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15]([NH2:17])=[S:16])[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=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][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 22459682(3-Methoxy-4-oxazol-5-yl-phenyl)-thiourea

Product 1

HCID 57780726(3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (74.8 mg, 0.3 mmol) and of 2-bromo-6-phenyl-cyclohexanone (75.9 mg, 0.3 mmol, preparation: WO9404487) in ethanol (4 mL) was heated over night 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/methanol (19:1 v/v) as eluent to yield the title compound (101 mg, 83%) as an off-white foam. MS ISP (m/e): 404.5 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.29 (s, 1H), 8.31 (s, 1H), 7.66 (s, 1H), 7.50 (d, 1H), 7.46-7.51 (m, 3H), 7.09-7.31 (m, 3H), 6.83 (s, 1H), 4.00 (m, 1H), 3.46 (s, 3H), 2.73 (m, 2H), 2.12 (m, 1H), 1.70-1.94 (m, 3H).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-f7d6574307724d029c3157fc7e6614fe
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Linked notes

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