Iodine → HCID 18670510, compound

HRID 1059305Notes

Reaction equation

HRID 1059305 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[SH:13])[C:6]([O:8][CH3:9])=[O:7].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.II.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1.CO>[N:16]1[C:17]2[NH:2][C:3]3[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:12]=3[S:13][C:18]=2[CH:19]=[CH:20][CH:15]=1

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 79772-ChloropyridineHCID 516892Sodium BicarbonateHCID 69807807HCID 69807807, compound

Product 1

HCID 18670510HCID 18670510, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

150 g of methyl 3-amino-4-mercaptobenzoate hydrochloride was suspended in 200 ml of diphenyl ether and heated to 100° C. After dropping 2-chloropyridine thereinto, 10.3 g of iodine was further added and the resulting mixture was reacted at 200° C. for 3 hours. After adding 20 ml of sulfuric acid and 300 ml of methanol at room temperature, the resulting mixture was heated under reflux for 3 hours. Then the reaction mixture was brought back to room temperature and poured into a cold saturated aqueous solution of sodium bicarbonate. Next, it was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The extract was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.3 g of the title compound as yellow crystals.

Workup

  1. customthe resulting mixture was reacted at 200° C. for 3 hours
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 3 hours
  4. customwas brought back to room temperature
  5. extractionNext, it was extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe extract was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-f0736bf3b24c42dda031c6af26134e14
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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