Water → C-(3-Chlorophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide

HRID 339863Notes

Reaction equation

HRID 339863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[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>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=2[O:14][CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 5972502,4-DimethoxybenzylamineHCID 2757802(3-Chlorophenyl)methanesulfonyl chloride

Product 1

HCID 68292460C-(3-Chlorophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1.06 g of 3-chlorophenylmethanesulfonyl chloride were initially charged in 30 ml of dichloromethane, and 1.42 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 water, 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 (1.65 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 (1.65 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-cb32bf059e5f47fa9f958260af0f0207
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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