1-(4-Ethoxycarbonylphenyl)-2-thiourea → HCID 57780714, compound

HRID 2075976Notes

Reaction equation

HRID 2075976 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[S:14])=[CH:8][CH:7]=1)=[O:5])C.Br[CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=O>C(O)C>[CH3:1][O:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[S:14][C:25]3[CH2:26][CH2:27][CH2:28][CH:23]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=4)[C:24]=3[N:15]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 28088481-(4-Ethoxycarbonylphenyl)-2-thioureaHCID 127791292-Bromo-6-phenylcyclohexanone

Product 1

HCID 57780714HCID 57780714, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-(4-ethoxycarbonylphenyl)-2-thiourea (105 mg, 0.5 mmol) and of 2-bromo-6-phenyl-cyclohexanone (253.1 mg, 1.00 mmol) in ethanol (4 mL) was heated for two days to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane. The product was precipitated with diethyl ether and heptane as an oil, which was purified on silica gel with dichloromethane as eluent to yield the title compound (120 mg, 63%) as a pale-yellow solid. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.42 (s, 1H), 7.77 (d, 2H), 7.50 (d, 2H), 7.28 (t, 2H), 7.27 (t, 1H), 7.12 (d, 2H), 4.23 (q, 2H), 4.06 (m, 1H), 2.73 (m, 2H), 2.12 (m, 1H), 1.70-1.90 (m, 3H), 1.27 (t, 3H).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. customThe product was precipitated with diethyl ether and heptane as an oil, which
  5. customwas purified on silica gel with dichloromethane as eluent

Sources & evidence

ORD record
ord-9d8422a9d503483a9040cc1baed90cec
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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