Hydrochloric Acid → HCID 12993820, compound

HRID 2183415Notes

Reaction equation

HRID 2183415 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:15]#[N:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].Cl>O1CCCC1.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:15]#[N:16])([C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[C:18]([F:17])([F:28])[F:29])[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 12993819HCID 12993819, compound

Product 1

HCID 12993820HCID 12993820, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.10 g (2.6 mmols) of sodium hydride was suspended in 20 ml of tetrahydrofuran. To the suspension was added dropwise, while stirring and cooling, 5 ml of a tetrahydrofuran solution in which 0.42 g (2.0 mmols) of methyl 2-(4-chlorophenyl)cyanoacetate and 0.41 g (2.6 mmols) of 2-trifluoromethylbenzoyl chloride had been dissolved. The mixture was stirred at room temperature over night. The reaction mixture was poured into ice water. The water phase thereof was acidified by diluted hydrochloric acid and twice extracted with 30 ml of ethyl acetate. The ethyl acetate extraction solutions were mixed, washed with a saturated brine solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue thus-obtained was purified by silica gel column chromatography (n-hexane:benzene=1:1), giving 0.45 g of the desired product (yield 59%).

Workup

  1. additionTo the suspension was added dropwise
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature over night
  4. extractiontwice extracted with 30 ml of ethyl acetate
  5. extractionThe ethyl acetate extraction solutions
  6. additionwere mixed
  7. washwashed with a saturated brine solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue thus-obtained
  11. customwas purified by silica gel column chromatography (n-hexane:benzene=1:1)

Sources & evidence

ORD record
ord-8592633c13384f60809b884312c8b334
Source dataset
uspto-grants-2005_05
Patent number
US06899886B2

Reaction notes

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