Diisopropylethylamine → 3-chloro-N,N-bis(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide

HRID 2168444Notes

Reaction equation

HRID 2168444 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[O:16][CH3:17].[Cl:24][C:25]1[CH:26]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[CH:29][C:30]=1[F:31].C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([S:32]([N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[O:16][CH3:17])[CH2:5][C:4]2[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:3]=2[O:2][CH3:1])(=[O:33])=[O:34])[CH:28]=[CH:29][C:30]=1[F:31]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 88696Bis(2,4-dimethoxybenzyl)amineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chloride

Product 1

HCID 672276373-chloro-N,N-bis(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(2,4-dimethoxybenzyl)amine (12 g) and 3-chloro-4-fluorobenzene-1-sulfonyl chloride (8.66 g) in dichloromethane (120 mL) was added N,N-diisopropylethylamine (13.5 mL) and catalytic amount of 4-dimethylaminopyridine. The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (600 mL) and washed with 5% aqueous HCl, water and brine. After drying over Na2SO4, the mixture was filtered and the filtrate was concentrated under vacuum to give crude product which was loaded on a 400 g silica gel column and eluted with 30% ethyl acetate in hexane to give the title compound.

Workup

  1. washwashed with 5% aqueous HCl, water and brine
  2. dry with materialAfter drying over Na2SO4
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customto give crude product which
  6. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fd44a0cbff3648e8ae6dce1e42f144d9
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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