Benzoic acid, 2-(chlorosulfonyl)-, methyl ester → Methyl 2-[(4-methoxypyridin-3-yl)sulfamoyl]benzoate

HRID 252212Notes

Reaction equation

HRID 252212 reaction equation
CO[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.Cl[S:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12].[C:24]([O-])(O)=[O:25].[Na+]>N1C=CC=CC=1>[CH3:24][O:25][C:4]1[CH:3]=[CH:8][N:7]=[CH:6][C:5]=1[NH:9][S:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 516892Sodium BicarbonateHCID 127035955-Methoxypyridin-3-ylamine

Product 1

HCID 46941843Methyl 2-[(4-methoxypyridin-3-yl)sulfamoyl]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-methoxypyridin-3-amine (1 eq) in pyridine (0.4 M) was added methyl 2-(chlorosulfonyl)benzoate (1 eq) and the mixture was stirred overnight at room temperature. The mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography to give afford the title compound. 1H NMR (400 MHz, DMSO-D6) δ 9.35-9.57 (m, 1H) 8.54-8.61 (m, 1H) 8.17-8.23 (m, 1H) 7.74-7.85 (m, 2H) 7.61-7.73 (m, 1H) 7.32-7.42 (m, 1H) 6.91-7.00 (m, 1H) 3.73 (s, 3H) 3.51 (s, 3H)

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography
  6. customto give

Sources & evidence

ORD record
ord-211cb20947c84e3ca7912fdc4f6f0e55
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Reaction notes

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