Benzoyl chloride → HCID 86723526, compound

HRID 2201292Notes

Reaction equation

HRID 2201292 reaction equation
[CH2:1]([N:3]1[C:8]([CH3:9])=[CH:7][C:6](=[O:10])[N:5]([CH2:11][CH3:12])[C:4]1=[O:13])[CH3:2].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Sn](Cl)(Cl)(Cl)Cl.ClC1C=CC=CC=1>CCOC(C)=O>[C:14]([C:7]1[C:6](=[O:10])[N:5]([CH2:11][CH3:12])[C:4](=[O:13])[N:3]([CH2:1][CH3:2])[C:8]=1[CH3:9])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 7964ChlorobenzeneHCID 24287Tin tetrachlorideHCID 12357931HCID 12357931, compound

Product 1

HCID 86723526HCID 86723526, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,3-Diethyl-6-methylpyrimidine-2,4(1H,3H)-dione (step 1)(680 mg, 3.73 mmol), benzoyl chloride (1.299 mL, 11.20 mmol) and tin(IV) chloride (1.314 mL, 11.20 mmol) were combined in chlorobenzene (30 mL, 295 mmol) and the mixture heated at reflux for 16 h. The reaction mixture was cooled to RT and diluted with EtOAc. The mixture was washed with 2M NaOH(aq) until basic. The organic phase was washed with brine, dried over sodium sulphate and evaporated under vacuum. The residue was dissolved in DCM and evaporated onto silica. The silica was deposited onto a 10 g silica cartridge and the system eluted with 10% EtOAc/hexane, 20% EtOAc/hexane, 40% EtOAc/hexane and 50% EtOAc/hexane. Product elutes at 40% EtOAc/hexane. Fractions were concentrated under vacuum to yield the title compound as an off white solid;

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  3. washThe mixture was washed with 2M NaOH(aq) until basic
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under vacuum
  7. dissolutionThe residue was dissolved in DCM
  8. customevaporated onto silica
  9. washthe system eluted with 10% EtOAc/hexane, 20% EtOAc/hexane, 40% EtOAc/hexane and 50% EtOAc/hexane
  10. concentrationFractions were concentrated under vacuum

Sources & evidence

ORD record
ord-4ae6386b76ea401c939dd7fde3f0fed5
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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