Methanesulfonamide → HCID 56592789, compound

HRID 2359269Notes

Reaction equation

HRID 2359269 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 72879MethanesulfonamideHCID 58046324HCID 58046324, compound

Product 1

HCID 56592789HCID 56592789, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-[(3,4-dichlorophenyl)sulfanyl]benzoic acid (Preparation 151, 200 mg, 0.67 mmol) in dichloromethane (5 mL) was added methanesulphonamide (192 mg, 2.01 mmol), 4-dimethylaminopyridine (245 mg, 2.01 mmol) and N-(3-dimethylaminopropyl)-M-ethylcarbodiimide hydrochloride (384 mg, 2.01 mmol) and the mixture was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane, washed with 1M hydrochloric acid solution and water, dried over Na2SO4 and the solvent evaporated in vacuo. The crude product was purified by preparative HPLC to afford the title compound as a white solid (34 mg, 12%).

Workup

  1. washwashed with 1M hydrochloric acid solution and water
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0f67023b943e4fa78cbdb5ba7590a2d8
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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