Water → N-(2,4-Dimethoxybenzyl)-C-o-tolylmethanesulfonamide

HRID 339850

Reaction equation

HRID 339850 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][S:8](Cl)(=[O:10])=[O:9].[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].O.C(OCC)(=O)C>ClCCl>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH:18][S:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:12])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 5972502,4-DimethoxybenzylamineHCID 2760661(2-methylphenyl)methanesulfonyl Chloride

Product 1

HCID 68291409N-(2,4-Dimethoxybenzyl)-C-o-tolylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1.00 g of o-tolylmethanesulfonyl chloride was initially charged in 30 ml of dichloromethane, and 1.46 ml of 2,4-dimethoxybenzylamine were added dropwise. The reaction mixture was stirred for 30 minutes. Then the mixture was admixed with 50 ml of water and 50 ml of ethyl acetate, and then the aqueous phase was washed once more with 30 ml of ethyl acetate. The combined organic phases were washed with 1 N aqueous hydrochloric acid, dried over MgSO4 and concentrated by rotary evaporation. The residue (1.42 g) was used in the next reaction without further purification.

Workup

  1. washthe aqueous phase was washed once more with 30 ml of ethyl acetate
  2. washThe combined organic phases were washed with 1 N aqueous hydrochloric acid
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue (1.42 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-bdd0e880a8d546f2bc7409c553806ba2
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Linked notes

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