2,4-Dimethoxybenzylamine → C-(3-Bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide

HRID 339834Notes

Reaction equation

HRID 339834 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][S:6](Cl)(=[O:8])=[O:7].[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]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][S:6]([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:8])=[O:7])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 2761451(3-bromophenyl)methanesulfonyl Chloride

Product 1

HCID 68292274C-(3-Bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While cooling with ice, 9.90 g of 3-bromobenzylsulfonyl chloride were initially charged in 120 ml of dichloromethane, and a solution of 11.55 ml of 2,4-dimethoxybenzylamine in 60 ml of dichloromethane was added dropwise within 15 minutes. The reaction mixture was allowed to come to room temperature and stirred for 1 hour. Subsequently, the mixture was washed with 50 ml of water, with 100 ml of 1 N aqueous hydrochloric acid, with 100 ml of saturated aqueous sodium hydrogencarbonate solution and finally once more with 100 ml of water. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue (14.30 g) was used in the next reaction without further purification.

Workup

  1. customto come to room temperature
  2. washSubsequently, the mixture was washed with 50 ml of water, with 100 ml of 1 N aqueous hydrochloric acid, with 100 ml of saturated aqueous sodium hydrogencarbonate solution and finally once more with 100 ml of water
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue (14.30 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-ea1f3e3aa0b049579333607fb37f4ba8
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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