Water → Dibenzo(b,f)thiepin, 3-methoxy-10-methyl-11-phenyl-

HRID 2296912Notes

Reaction equation

HRID 2296912 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:7]([CH2:15]CC(O)=O)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1.[H-].[Na+].O.[CH3:31]N(C)C=O>C1(C)C=CC=CC=1>[CH3:31][O:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:7]([CH3:15])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 18388757HCID 18388757, compound

Product 1

HCID 55148Dibenzo(b,f)thiepin, 3-methoxy-10-methyl-11-phenyl-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-hydroxy-11-[(2-carboxy)ethyl]-10-phenyldibenzo[b,f]thiepin (1.87 g) in dry dimethylformamide (25 ml) was treated with sodium hydride (0.4 g of 75%) and stirred, first at room temperature and then at 50° C. until effervescence ceased. A solution of 1-chloro-2-NN-dimethylamino-ethane in toluene (15 ml of 1 M) was added and the mixture was heated with stirring under argon to 100° C. After 1.5 hours the mixture was allowed to cool, treated with water and extracted three times with ethyl acetate. The ethyl acetate solution was evaporated and the residue dissolved in methanol (10 ml) and 10% aqueous sodium hydroxide (5 ml) and refluxed for 20 minutes. The solvent was mostly removed and the sodium salt was dissolved in 200 ml of boiling water. Carbon dioxide was passed through the boiling solution until the pH fell to 8. This was extracted three times into ethyl acetate with a little methanol. The solution was dried and evaporated.

Workup

  1. customat 50° C.
  2. temperaturethe mixture was heated
  3. stirringwith stirring under argon to 100° C
  4. temperatureto cool
  5. extractionextracted three times with ethyl acetate
  6. customThe ethyl acetate solution was evaporated
  7. dissolutionthe residue dissolved in methanol (10 ml)
  8. temperature10% aqueous sodium hydroxide (5 ml) and refluxed for 20 minutes
  9. customThe solvent was mostly removed
  10. dissolutionthe sodium salt was dissolved in 200 ml of boiling water
  11. extractionThis was extracted three times into ethyl acetate with a little methanol
  12. customThe solution was dried
  13. customevaporated

Sources & evidence

ORD record
ord-753cf7cf5f3d4a8ca892f98f9aa70783
Source dataset
uspto-grants-2002_12
Patent number
US06489481B1

Reaction notes

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