Sulfuric Acid → HCID 66877977, compound

HRID 1364899Notes

Reaction equation

HRID 1364899 reaction equation
N[C:2]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:25].[K+]>O>[I:25][C:2]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 22620941158580-87-1HCID 23668193Sodium Nitrite

Product 1

HCID 66877977HCID 66877977, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

600 mg of methyl 2-amino-4-(methylsulfonyl)benzoate was added to a solution of 4 mL of H2O and 1 mL of concentrated sulfuric acid. The solution was cooled to 0° C. and a solution of 206 mg of sodium nitrite in 1 mL of H2O was added slowly. The reaction mixture was stirred for 2 h and then a solution of 782 mg of potassium iodide in 2 mL of H2O was added dropwise at 0° C. The reaction was allowed to warm to room temperature and stirred for 5 h. The mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated Na2S2O3, dried (MgSO4) and evaporated. Purified by silica gel chromatography (5-50% ethyl acetate/hexane) to afford methyl 2-iodo-4-(methylsulfonyl)benzoate. 160 mg of methyl 2-iodo-4-(methylsulfonyl)benzoate was hydrolyzed via Procedure M to give 2-iodo-4-(methylsulfonyl)benzoic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-iodo-4-(methylsulfonyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-iodo-4-(methylsulfonyl)benzamide. MS (Q1) 513.0 (M)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 5 h
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with saturated Na2S2O3
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurified by silica gel chromatography (5-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4bdff88c011d4600a4b180fc537f3df4
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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