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

HRID 1387972Notes

Reaction equation

HRID 1387972 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]([CH2:29]O)=[CH:25][CH:24]=4)=[O:21])=[CH:15][C:14]=3[CH:31]=2)=[CH:6][CH:5]=1)[CH3:2].S(Cl)([Cl:34])=O.O>N1C=CC=CC=1.C(Cl)(Cl)Cl.C1COCC1.C(OCC)(=O)C>[Cl:34][CH2:29][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:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=4)=[CH:31][C:14]=3[CH:15]=2)=[O:21])=[CH:24][CH:25]=1

Participants

8

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 184723397-(4-ethoxyphenyl)-N-(4-hydroxymethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

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

Reagents, catalysts & solvents 4

HCID 1049PyridineCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 7-(4-ethoxyphenyl)-N-(4-hydroxymethylphenyl)-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 diisopropylether 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 diisopropylether

Sources & evidence

ORD record
ord-83c3a2e7e4f84188bb31fdeeeea2ad64
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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