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

HRID 2076129Notes

Reaction equation

HRID 2076129 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[C:9]1[S: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[C:9]1[S:13][C:12]([CH3:14])=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632612[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-thiourea

Product 1

HCID 44193860[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [3-methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-thiourea (110 mg, 0.39 mmol) and 2-bromo-6-phenyl-cyclohexanone (105 mg, 0.41 mmol) in ethanol (4 ml) was heated to reflux over night. The precipitated solid was filtered off after cooling to room temperature and dried to yield the title compound (160 mg, 94%) as a yellow solid. MS ISP (m/e): 434.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.32 (br s, 1H, NH), 8.10 (s, 1H), 7.61 (s, 1H), 7.56 (d, 1H), 7.29 (t, 2H), 7.15-7.21 (m, 3H), 6.85 (d, 1H), 4.00 (m, 1H), 3.48 (s, 3H), 2.75 (m, 2H), 2.68 (s, 3H), 2.14 (m, 1H), 1.70-1.94 (m, 3H).

Workup

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-7033ec88da9844b78e86bbcc5424bc2e
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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