Triethylamine → HCID 23121853, compound

HRID 1713571Notes

Reaction equation

HRID 1713571 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].S(Cl)(Cl)=O.C(N(CC)CC)C.[C:23]1([C:29]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:33]3[CH2:34][NH:35][CH2:36][CH2:37][N:32]3[C:31](=[O:38])[O:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.O1CCCC1.O>[O:38]=[C:31]1[N:32]2[CH2:37][CH2:36][N:35]([C:6]([C:5]3[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=3)[CH:1]=[O:2])=[O:8])[CH2:34][CH:33]2[C:29]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:30]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 120773-CarboxybenzaldehydeHCID 24386Thionyl ChlorideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121853HCID 23121853, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Formylbenzoic acid (0.10 g, 0.67 mmol) was dissolved in toluene (7 mL). Thionyl chloride (0.80 g, 6.7 mmol) was added thereto, and the mixture was heated under reflux for 1 hour. The reaction solution was concentrated, and the residue was dissolved in tetrahydrofuran (5 mL). The resulting solution was added dropwise to a solution of triethylamine (69 mg, 0.68 mmol) and hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.68 mmol) in tetrahydrofuran (3 mL) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was sequentially washed with 1 N hydrochloric acid, an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate), and the fractions were collected and concentrated. The residue was collected by filtration and washed with diisopropyl ether to obtain the title compound (0.19 g, yield 66%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction solution was concentrated
  4. dissolutionthe residue was dissolved in tetrahydrofuran (5 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was sequentially washed with 1 N hydrochloric acid
  7. dry with materialan aqueous saturated sodium hydrogen carbonate solution, water and saturated brine, and dried over magnesium sulfate
  8. filtrationThe solid was filtered off
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  11. customthe fractions were collected
  12. concentrationconcentrated
  13. filtrationThe residue was collected by filtration
  14. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-b5a671754dc04b8aa3cc3d51eb651ec9
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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