Hydrochloric Acid → HCID 21511892, compound

HRID 1576320Notes

Reaction equation

HRID 1576320 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[N:6]3[CH2:13][CH2:14][O:15][C:5]3([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:24]I.Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:24])[C:7](=[O:12])[N:6]3[CH2:13][CH2:14][O:15][C:5]3([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12750804HCID 12750804, compound

Product 1

HCID 21511892HCID 21511892, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g of 9-chloro-2,3,6,10b-tetrahydro-10b-phenyl-5H-oxazolo[3,2-C]quinazolin-5-one in 20 ml of dimethylformamide was added 0.21 g of 62.5% sodium hydride. The resultant mixture was stirred with heating at 50° - 55°C for 1 hour, and 1.42 g of methyl iodide was added thereto at room temperature. Then, the mixture was heated at 55° - 60°C for 3 hours. After cooling, the reaction mixture was poured into 100 ml of water and acidified with hydrochloric acid. The resulting mixture was extracted with 50 ml of chloroform and the chloroform layer was washed successively with dilute hydrochloric acid and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel using chloroform as an eluent to give 1.2 g of 9-chloro-2,3,6,10b-tetrahydro-6-methyl-10b-phenyl-5H-oxazolo[3,2-C]quinazolin-5-one, having a melting point of 124° - 125°C. Recrystallization from ethanol gave colorless prisms, having a melting point of 136° - 137°C.

Workup

  1. temperaturewith heating at 50° - 55°C for 1 hour
  2. customat room temperature
  3. temperatureThen, the mixture was heated at 55° - 60°C for 3 hours
  4. temperatureAfter cooling
  5. extractionThe resulting mixture was extracted with 50 ml of chloroform
  6. washthe chloroform layer was washed successively with dilute hydrochloric acid and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8664b2baaee740889de5219e39318ab2
Source dataset
uspto-grants-1976_09
Patent number
US03980645

Reaction notes

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