Sodium Carbonate → HCID 11232153, compound

HRID 2243212Notes

Reaction equation

HRID 2243212 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1>CCCCCC.C(OCC)(=O)C.CN1C(=O)CCC1>[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][C:2]2[CH:3]=[C:4]([C:8]3([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 145104-AminothiophenolHCID 114597874-(3-bromophenyl)oxane-4-carbonitrile

Product 1

HCID 11232153HCID 11232153, compound

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-(3-bromophenyl)tetrahydro-2H-pyran-4-carbonitrile (5.0 g, 18.79 mmol) (example 3), sodium carbonate (13.94 g, 131.58 mmol) and cesium carbonate (9.18 g, 28.19 mmol) was evacuated under vacuum for about 15 minutes. N-methyl pyrrolidinone (35 mL) and 4-aminothiophenol (2.8 g, 22.57 mmol) were added to this mixture under nitrogen atmosphere and heated at about 130° C. for about 15 hours. The reaction mixture was cooled to room temperature, poured over ice water and stirred. The mixture was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum to afford a brownish residue. Column chromatography over silica gel using ethyl acetate and hexane (3:2) yielded the title compound as a light yellow solid. Yield: 6.2 g.

Workup

  1. customwas evacuated under vacuum for about 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customto afford a brownish residue

Sources & evidence

ORD record
ord-44057644967b431680d830839a2c29d0
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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