Benzaldehyde → HCID 22674379, compound

HRID 1005707Notes

Reaction equation

HRID 1005707 reaction equation
Cl[C:2]1[C:3]2[S:14][CH:13]=[CH:12][C:4]=2[N:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].C[N+]1(C)C=CN=C1.[H-].[Na+]>C1COCC1.O>[C:16]1([C:15]([C:2]2[C:3]3[S:14][CH:13]=[CH:12][C:4]=3[N:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=2)=[O:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 136858841,1-Dimethyl-1H-imidazol-1-ium iodideHCID 226743734-Chloro-2-(trifluoromethyl)thieno[3,2-d]pyrimidine

Product 1

HCID 22674379HCID 22674379, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-chloro-2-trifluoromethylthieno[3,2-d]pyrimidine (0.3 g, 1.26 mmol), benzaldehyde (0.28 g, 2.64 mmol) and N,N-dimethylimidazolium iodide (0.2 g, 0.89 mmol) in THF (8 mL) was treated with NaH (60% dispersion in oil, 0.112 g, 2.8 mmol), refluxed for 15 min, cooled to room temperature, treated with water (4 mL) and the organic phase separated. The aqueous phase was extracted with CH2Cl2 (2×20 mL), the combined organic phase washed with brine (10 mL), dried (MgSO4), concentrated in vacuo and the resulting brown oil purified by chromatography [SiO2; heptane-EtOAc (3:1)] then recrystallised from heptane to give the title compound (280 mg, 43%) as yellow needles.

Workup

  1. temperaturerefluxed for 15 min
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 mL)
  4. washthe combined organic phase washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting brown oil purified by chromatography [SiO2; heptane-EtOAc (3:1)]
  8. customthen recrystallised from heptane

Sources & evidence

ORD record
ord-2c70b2d3400a463ebfde38c88cd8187e
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

Loading…