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

HRID 339878Notes

Reaction equation

HRID 339878 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:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:16]=1[CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29].C(N(CC)C(C)C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][S:6]([N:18]([CH2:17][C:16]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:15]=2[O:14][CH3:13])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])(=[O:8])=[O:7])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 88696Bis(2,4-dimethoxybenzyl)amineHCID 2761451(3-bromophenyl)methanesulfonyl Chloride

Product 1

HCID 68292386C-(3-Bromophenyl)-N,N-bis(2,4-dimethoxybenzyl)methanesulfonamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

While cooling with ice, 4.94 g of 3-bromobenzylsulfonyl chloride were initially charged in 60 ml of dichloromethane and, within 15 minutes, a solution of 5.64 g of bis(2,4-dimethoxybenzyl)amine in 30 ml of dichloromethane and then a solution of 3.82 ml of N,N-diisopropylethylamine in 5 ml of dichloromethane were added dropwise. 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 50 ml of 1 N aqueous hydrochloric acid, with 50 ml of saturated aqueous sodium hydrogencarbonate solution and finally with 50 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (9.23 g) with a molecular weight of 550.5 g/mol (C25H28BrNO6S).

Workup

  1. customto come to room temperature
  2. washSubsequently, the mixture was washed with 50 ml of water, with 50 ml of 1 N aqueous hydrochloric acid, with 50 ml of saturated aqueous sodium hydrogencarbonate solution and finally with 50 ml of saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by means of normal phase chromatography
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d7b2e933588d40b99a807b116b86b72f
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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