4-Chlorobenzaldehyde → HCID 13105884, compound

HRID 1642368Notes

Reaction equation

HRID 1642368 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:11][CH:10]=[CH:9][N:5]2[C:6](=[O:8])[CH:7]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[O-]CC.[Na+]>C(O)C>[Cl:12][C:13]1[CH:20]=[CH:19][C:16](/[CH:17]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:11][CH:10]=[CH:9][N:5]3[C:6](=[O:8])[CH:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-oneHCID 2723922Sodium ethoxide

Product 1

HCID 13105884HCID 13105884, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of Step 1 intermediate (200 mg, 1.206 mmol) in ethanol (30 ml) was added 4-chlorobenzaldehyde (253 mg, 1.795 mmol) followed by sodium ethoxide (122 mg, 1.795 mmol) in ethanol at room temperature. The reaction mixture was heated to reflux for 12 h. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue obtained was partitioned between chloroform (100 ml) and water (50 ml). The organic layer was washed with brine (100 ml), dried (Na2SO4) and concentrated to afford a crude product which was purified by silica gel column chromatography using 2% acetone in chloroform to give 59 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 6.25 (s, 1H), 6.87 (d, J=15.6 Hz, 1H), 6.94 (d, J=4.8 Hz, 1H), 7.33 (d, J=9.0 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.73 (d, J=15.6 Hz, 1H), 7.90 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 289.37 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customwas partitioned between chloroform (100 ml) and water (50 ml)
  6. washThe organic layer was washed with brine (100 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto afford a crude product which
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-52cb1d9c95894a94804927a9cfef4e47
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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