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

HRID 1870517Notes

Reaction equation

HRID 1870517 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-2b7fb6c8c4b84e5d98c3b64630dc7302
Source dataset
uspto-grants-2000_08
Patent number
US06096780

Reaction notes

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