2-Bromo-6-phenylcyclohexanone → (4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amine

HRID 2076135Notes

Reaction equation

HRID 2076135 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)=[CH:3][CH:2]=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>[C:20]1([CH:24]2[C:25]3[N:16]=[C:14]([NH:13][C:10]4[CH:9]=[CH:8][C:7]([C:4]5[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=5)=[CH:12][CH:11]=4)[S:15][C:26]=3[CH2:27][CH2:28][CH2:29]2)[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632614(4-Pyridin-4-yl-phenyl)-thiourea

Product 1

HCID 44194155(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amineYield 20.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-pyridin-4-yl-phenyl)-thiourea (100 mg, 0.44 mmol) and 2-bromo-6-phenyl-cyclohexanone (116 mg, 0.46 mmol) in ethanol (5 ml) was heated to reflux over night. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as the eluent to yield the title compound (34 mg, 20%) as a yellow solid. MS ISP (m/e): 384.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=8.61 (d, 2H), 7.59 (d, 2H), 7.46 (d, 1H), 7.18-7.33 (m, 5H), 7.13 (d, 2H), 4.08 (m, 1H), 2.75 (m, 2H), 2.18 (m, 1H), 1.7-1.98 (m, 3H).

Workup

  1. temperatureto reflux over night
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b5c3ab6531d04e63bf00583ca60bc0de
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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