2,4-Dimethoxybenzylamine → HCID 68292190, compound

HRID 2405689Notes

Reaction equation

HRID 2405689 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=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]>ClCCl>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][S:7]([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:9])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 5987644-Bromobenzylsulfonyl chloride

Product 1

HCID 68292190HCID 68292190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

While cooling with ice, 20.0 g of 4-bromobenzylsulfonyl chloride were initially charged in 200 ml of dichloromethane, and a solution of 24 ml of 2,4-dimethoxybenzylamine in 100 ml of dichloromethane was slowly added dropwise. For improved stirrability, a further 100 ml of dichloromethane were added, and the reaction mixture was allowed to come to room temperature. After stirring for 2 hours, the reaction mixture was washed with 100 ml of water, with 100 ml of 0.2 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 Na2SO4, concentrated by rotary evaporation and dried under high vacuum. The residue (30 g) was used in the next reaction without further purification.

Workup

  1. customto come to room temperature
  2. washthe reaction mixture was washed with 100 ml of water, with 100 ml of 0.2 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 Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customdried under high vacuum
  6. customThe residue (30 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-df87379b11704a5a9ad7ae50ba24acd1
Source dataset
uspto-grants-2014_08
Patent number
US08809324B2

Reaction notes

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