Acetic Acid → N-(2,4-Dimethoxybenzyl)-1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide

HRID 339835Notes

Reaction equation

HRID 339835 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C[Li].[CH3:26][C:27]([CH3:29])=[O:28].C(O)(=O)C>C1COCC1.C(OCC)C.C(OCC)(=O)C>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][S:9]([CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:27]([OH:28])([CH3:29])[CH3:26])(=[O:10])=[O:11]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 68292274C-(3-Bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamideHCID 178418348HCID 178418348, compound

Product 1

HCID 68291617N-(2,4-Dimethoxybenzyl)-1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under inert gas, 7.00 g of C-(3-bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide were initially charged in 120 ml of THF, and then, at a temperature of −78° C., 25.14 ml of a 1.6 N methyllithium solution in diethyl ether were added dropwise and the mixture was stirred at constant temperature for 10 minutes. Subsequently, 7 ml of acetone were added. After stirring for 5 minutes, the reaction solution was admixed with 5 ml of acetic acid and stirred for a further 5 minutes, and 100 ml of ethyl acetate were added to the mixture, which was washed with 1×100 ml and 1×50 ml of a saturated aqueous sodium hydrogencarbonate solution and 2×50 ml of a saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue (8.63 g) was used in the next reaction without further purification.

Workup

  1. stirringAfter stirring for 5 minutes
  2. stirringstirred for a further 5 minutes
  3. washwas washed with 1×100 ml and 1×50 ml of a saturated aqueous sodium hydrogencarbonate solution and 2×50 ml of a saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue (8.63 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-7ab3af89c4e24180bbd4dcb56a7c8fa5
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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