Hydrochloric Acid → HCID 12000685, compound

HRID 421557Notes

Reaction equation

HRID 421557 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[S:10])[NH2:9].C(=O)([O-])[O-].[Ca+2].Br[CH:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=O.Cl>CC(O)C>[C:20]1([C:18]2[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[S:10][C:17]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 2749469HCID 2749469, compoundHCID 57440257HCID 57440257, compound

Product 1

HCID 12000685HCID 12000685, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 183 mg portion of pyridine-2-carbothioamide hydrochloride and 209 mg of calcium carbonate were added at room temperature to a 2-propanol solution (20 ml) of 340 mg of 2-bromo-1-(1-naphthyl)-2-phenylethanone and heated overnight under reflux. The reaction liquid was acidified by adding 1 M hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography using ethyl acetate:n-hexane (1:9) as the elution solvent, thereby obtaining 227 mg of 2-[4-(1-naphthyl)-5-phenyl-1,3-thiazol-2-yl]pyridine as a colorless solid.

Workup

  1. temperatureheated overnight
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe thus obtained residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-5f22b9380e5e4d2cabc459309806fff3
Source dataset
uspto-grants-2012_01
Patent number
US08101580B2

Reaction notes

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