Diethyl bromomalonate → HCID 178470560, compound

HRID 1158089Notes

Reaction equation

HRID 1158089 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([NH2:12])=[S:11].CCN(C(C)C)C(C)C.Br[CH:25]([C:31](OCC)=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>CCO.CCOC(C)=O>[O:32]=[C:31]1[CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:11][C:10]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:13])([F:1])[F:14])=[N:12]1

Participants

6

Reactant 3

HCID 69637Diethyl bromomalonateHCID 81531DiisopropylethylamineHCID 737227Thiourea, [2-(trifluoromethyl)phenyl]-

Product 1

HCID 178470560HCID 178470560, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(trifluoromethyl)phenylthiourea (Menai Organics, 2.36 g, 10.7 mmol), Hunig's base (Aldrich, 1.9 mL, 10.7 mmol) in EtOH (10 mL) was added diethyl bromomalonate (2.0 mL, 10.7 mmol). After 1.5 h at room temperature, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. MS: 333 (M+1).

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-778c2f52c6ca40d59a23c32dcb67baff
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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