Pyridine → Dimethyl 5-(methylsulfonamido)isophthalate

HRID 2071117Notes

Reaction equation

HRID 2071117 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([NH:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 66831Dimethyl 5-aminoisophthalate

Product 1

HCID 3711983Dimethyl 5-(methylsulfonamido)isophthalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of dimethyl 5-aminoisophthalate (2.09 g, 10 mmol) in dichloromethane (30 mL), pyridine (2.43 mL, 30 mmol) was added at room temperature. At 0° C., methanesulfonyl chloride (0.86 mL, 11 mmol) was added and the resulting mixture was stirred overnight at room temperature. The reaction mixture was then concentrated under reduced pressure and ethyl acetate (50 mL) was added. The resulting white precipitate was filtered and washed with hexanes to give dimethyl 5-(methylsulfonamido)isophthalate in 95% (2.715 g) yield as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure and ethyl acetate (50 mL)
  2. additionwas added
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-b90934f443c944ea9297f7ab5c6cedf7
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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