Phenylmethanesulfonyl chloride → HCID 68292276, compound

HRID 339819Notes

Reaction equation

HRID 339819 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>ClCCl>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][S:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 68292276HCID 68292276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

While cooling with ice, 5.00 g of phenylmethanesulfonyl chloride were initially charged in 40 ml of dichloromethane, and a solution of 8.04 ml of 2,4-dimethoxybenzylamine in 10 ml of dichloromethane was slowly added dropwise. For improved stirrability, a further 25 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 (8.42 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 (8.42 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-0e88677568664e15b96ca33020192eec
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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