Toluene → HCID 86649793, compound

HRID 1967546Notes

Reaction equation

HRID 1967546 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[C:10]1(C)C=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:17][S:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])(=[O:20])=[O:19].C([O:33][CH2:34][CH3:35])(=O)C>>[CH3:1][O:2][C:3]1[C:4]([N:9]([C:34]([C:35]2[CH:10]=[C:11]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:12]=[CH:13][CH:14]=2)=[O:33])[C:24]([C:23]2[CH:22]=[C:21]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:29]=[CH:28][CH:27]=2)=[O:25])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 99203842-Amino-3-methoxypyridine

Product 1

HCID 86649793HCID 86649793, compoundYield 18%

Procedure

3-Methoxypyridine-2-amine (780 mg) was added to a toluene (50 mL) solution of 3-(chlorosulfonyl)benzoyl chloride (3.00 g), and stirred overnight at room temperature. Ethyl acetate was added to the reaction liquid, then washed twice with water and once with saturated brine, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=form 0% to 80%, gradient) to give the entitled compound (608 mg, 18%) as a white solid.

Workup

  1. washwashed twice with water and once with saturated brine
  2. dry with materialdried with sodium sulfate
  3. customThe drying agent was removed through filtration
  4. customthe solvent was evaporated off under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=form 0% to 80%, gradient)

Sources & evidence

ORD record
ord-5696e6b8e93d45f3b279da746ba25ba4
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

Loading…