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

HRID 2076133Notes

Reaction equation

HRID 2076133 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][C:9]=2[O:18][CH3:19])=[C:5]([CH3:7])[N:6]=1.Br[CH:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]1=O>C(O)C>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[S:16][C:29]4[CH2:30][CH2:31][CH2:32][CH:27]([C:23]5[CH:24]=[CH:25][CH:26]=[CH:21][CH:22]=5)[C:28]=4[N:17]=3)=[CH:10][C:9]=2[O:18][CH3:19])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632613[4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thiourea

Product 1

HCID 44193960[4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thiourea (88 mg, 0.30 mmol) and 2-bromo-6-phenyl-cyclohexanone (80 mg, 0.32 mmol) in ethanol (3 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 (100 mg, 100%) as a yellow solid. MS ISP (m/e): 448.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.27 (br s, 1H, NH), 7.59 (s, 1H), 7.28 (t, 2H), 7.12-7.19 (m, 4H), 6.85 (d, 1H), 4.00 (m, 1H), 3.37 (s, 3H), 2.74 (m, 2H), 2.66 (s, 3H), 2.20 (s, 2H), 2.13 (m, 1H), 1.70-1.93 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-d04d7e206a2040e7a43548a31c314d87
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

Loading…