Thionyl Chloride → N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 843105Notes

Reaction equation

HRID 843105 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1.S(Cl)([Cl:32])=O>N1C=CC=CC=1.C(Cl)(Cl)Cl.O>[Cl:32][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:13][CH2:14][O:15][C:16]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)=[CH:19][C:17]=3[CH:18]=2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 18472380N-(4-hydroxymethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

Product 1

HCID 18472316N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideYield 88%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N-(4-hydroxymethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (412 mg, 1.07 mmol) and pyridine (1 drop) in chloroform (5 ml) was dropwise added thionyl chloride (0.14 ml, 1.61 mmol), and the mixture was stirred for 2 hours. The mixture was diluted with water and extracted with chloroform. The extract was washed with saturated sodium chloride solution and dried with magnesium sulfate. The solvent was evaporated, and the resulting powder was washed with hexane-ethyl acetate (1:1) to give N-(4-chloromethylphenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (380 mg, 88%) as colorless powder.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe resulting powder was washed with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-19f28c0510de44e28b369d31ab27d852
Source dataset
uspto-grants-2002_04
Patent number
US06376536B1

Reaction notes

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