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

HRID 2076084Notes

Reaction equation

HRID 2076084 reaction equation
[CH3:1][C:2]1[O:3][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:5][N: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[O:3][C:4]([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:5][N:6]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632608[4-(2-Methyl-oxazol-5-yl)-phenyl]-thiourea

Product 1

HCID 44193858[4-(2-Methyl-oxazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(2-methyl-oxazol-5-yl)-phenyl]-thiourea (100 mg, 0.43 mmol) and 2-bromo-6-phenyl-cyclohexanone (114 mg, 0.45 mmol) in ethanol (5 mL) was heated to reflux over night. The solvent was removed under reduced pressure and the residue purified on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as eluent to yield the title compound (73 mg, 44%) as a yellow gum. MS ISP (m/e): 388.2 (100%) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.18 (s, 1H), 7.49 (m, 4H), 7.11-7.29 (m, 6H), 4.04 (m, 1H), 2.70 (m, 2H), 2.43 (s, 3H), 2.14 (m, 1H), 1.70-1.93 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-6875cb15b25f4a42976a261b06b90417
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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