2-Bromo-6-phenylcyclohexanone → N-[3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-4-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine

HRID 2075985Notes

Reaction equation

HRID 2075985 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:28]3[CH2:29][CH2:30][CH2:31][CH:26]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:20][CH:21]=4)[C:27]=3[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 42647277N-[3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-4-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-amineYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (131.2 mg, 0.5 mmol) and of 2-bromo-6-phenyl-cyclohexanone (139.2 mg, 0.55 mmol) in ethanol (5 mL) was stirred at room temperature over the weekend. A clear yellow solution was obtained which 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 by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (110 mg, 53%) as a white solid. MS ISP (m/e): 417.5 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.19 (s, 1H), 7.66 (s, 1H), 7.57 (s, 1H), 7.27 (t, 2H), 7.11-7.18 (m, 4H), 6.95 (s, 1H), 6.71 (d, 1H), 3.98 (m, 1H), 3.34 (s, 3H), 2.73 (m, 2.14 (m, 1H), 2.10 (s, 3H), 1.70-1.91 (m, 3H).

Workup

  1. customA clear yellow solution was obtained which
  2. temperaturewas heated over night
  3. temperatureto reflux under an atmosphere of nitrogen
  4. customwas evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b01aec049334137959bb57ca070d3ec
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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