Water → N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 2228233Notes

Reaction equation

HRID 2228233 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][C:16]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26](O)=[CH:25][C:24]=4C)=[O:21])=[CH:15][C:14]=3[CH:31]=2)=[CH:6][CH:5]=1)[CH3:2].S(Cl)(Cl)=O.O.[CH:37](Cl)(Cl)[Cl:38]>N1C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[Cl:38][CH2:37][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]([C:16]2[CH2:17][CH2:18][O:19][C:13]3[CH:12]=[CH:11][C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=4)=[CH:31][C:14]=3[CH:15]=2)=[O:21])=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 70161845HCID 70161845, compound

Product 1

HCID 18472558N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 7-(4-ethoxyphenyl)-N-(4-hydroxy-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (2.55 g) and pyridine (2 drops) in chloroform (50 ml) was added thionyl chloride (0.8 ml) at room temperature, and the mixture was stirred for 20 hours. To the reaction mixture was added water and then THF, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to give solid, which was dissolved in THF and ethyl acetate. The mixture was concentrated under reduced pressure to give crystals, which were collected by filtration and washed with dusopropylether to give N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (2.42 g) as colorless crystals.

Workup

  1. extractionTHF, and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give solid, which
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customto give crystals, which
  8. filtrationwere collected by filtration
  9. washwashed with dusopropylether

Sources & evidence

ORD record
ord-590103e8ab674fc588fc187cb6092fa7
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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