Methanesulfonyl chloride → HCID 5303011, compound

HRID 1776532Notes

Reaction equation

HRID 1776532 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[NH:1][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2734814Methyl 3-Amino-4-methoxybenzoate

Product 1

HCID 5303011HCID 5303011, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 3-amino-4-methoxybenzoate (0.509 g, 2.81 mmol) in pyridine (10 ml), methanesulfonyl chloride (0.285 ml, 3.65 mmol) was added drop wise and the mixture was stirred at RT for 2 hours. The solvent was removed under vacuum, and the crude was portioned between EtOAc and HCl 1N. The organic phase was dried over Na2SO4 and the solvent was removed. The crude was purified by filtration through a silica gel cartridge (DCM:EtOAc=90:10) to give methyl 4-methoxy-3-(methylsulfonamido)benzoate (0.673 g, 2.60 mmol, 92% yield, MS/ESI+ 259.9 [MH]+).

Workup

  1. customThe solvent was removed under vacuum
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed
  4. filtrationThe crude was purified by filtration through a silica gel cartridge (DCM:EtOAc=90:10)

Sources & evidence

ORD record
ord-f5f000e2cc8f41469d74a50aca36d380
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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