Methanesulfonyl chloride → HCID 71714815, compound

HRID 520972Notes

Reaction equation

HRID 520972 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=1)(=[O:17])=[O:16].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([S:6][CH2:5][C:4]2[CH:27]=[CH:28][CH:29]=[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[CH:3]=2)=[C:8]([NH:14][S:15]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[CH:22]=2)(=[O:17])=[O:16])[CH:9]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67972007N-{2-[(3-aminobenzyl)sulfanyl]-5-chlorophenyl}-1-benzofuran-2-sulfonamide

Product 1

HCID 71714815HCID 71714815, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{2-[(3-aminobenzyl)sulfanyl]-5-chlorophenyl}-1-benzofuran-2-sulfonamide (440 mg, 0.90 mmol) in pyridine (4 ml) was added methanesulfonyl chloride (70 μl, 0.90 mmol). The reaction was stirred at room temperature for 2 hours and was concentrated, diluted with 1M HCl, and extracted with EtOAc. The organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (4% EtOAc in hexane) to yield the title compound (344 mg, 67%).

Workup

  1. concentrationwas concentrated
  2. additiondiluted with 1M HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (4% EtOAc in hexane)

Sources & evidence

ORD record
ord-e1f17127ccd849aa854ed40a8f93cd36
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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