Methanesulfonamide → 4-(3,4-Dichlorobenzyl)-N-(methylsulfonyl)benzamide

HRID 2359268Notes

Reaction equation

HRID 2359268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1.[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580463204-(3,4-Dichlorobenzyl)benzoic acid

Product 1

HCID 565927904-(3,4-Dichlorobenzyl)-N-(methylsulfonyl)benzamideYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(3,4-dichlorobenzyl)benzoic acid (Preparation 148,150 mg, 0.54 mmol) in dichloromethane (25 mL) was added methanesulphonamide (153 mg, 1.61 mmol), 4-dimethylaminopyridine (196 mg, 1.61 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (307 mg, 1.61 mmol) and the mixture was stirred at room temperature for 5 hours. The mixture was diluted with dichloromethane, washed with water and 1M hydrochloric acid solution, dried over Na2SO4 and the solvent evaporated in vacuo. The crude product was purified by silica gel column chromatography eluting with 95:5 dichloromethane:methanol to afford the title compound (102 mg, 53%).

Workup

  1. washwashed with water and 1M hydrochloric acid solution
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by silica gel column chromatography
  5. washeluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-4998dc2f4a424ce08fd18137f4d9130e
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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