Hydrogen Peroxide → (6-Benzenesulfonyl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid methyl ester

HRID 839631Notes

Reaction equation

HRID 839631 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:10][N:9]2[CH:22]=1)=[O:4].FC(F)(F)C(OO)=[O:26].FC(F)(F)C(OC(=O)C(F)(F)F)=O.OO>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:26])=[O:15])=[CH:10][N:9]2[CH:22]=1)=[O:4]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 191716Methyl 6-(phenylsulfinyl)imidazo(1,2-a)pyridine-2-carbamateHCID 10290812Trifluoroperacetic acid

Product 1

HCID 12414301(6-Benzenesulfonyl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Portionwise, with cooling, 0.500 g. (0.0015 mole) of 2(methoxycarbonylamino)-6-(phenylsulfinyl) imidazo [1,2-a] pyridine is added to 5 ml. of a methylene chloride solution of trifluoroperacetic acid prepared from 415 μl. trifluoroacetic anhydride and 65 μl. of 90% hydrogen peroxide. The solution is heated at reflux for 20 hours. The cooled reaction mixture is washed with 10 ml. of a saturated aqueous sodium bicarbonate solution, the organic layer is separated and chromatographed on silica gel. Elution with 50% ethyl acetate-methylene chloride yields 2-(methoxycarbonylamino) 6-(phenylsulfonyl) imidazo [1,2-a] pyridine, m.p. 300° C.

Workup

  1. temperaturePortionwise, with cooling
  2. temperatureThe solution is heated
  3. temperatureat reflux for 20 hours
  4. customThe cooled reaction mixture
  5. washis washed with 10 ml
  6. customof a saturated aqueous sodium bicarbonate solution, the organic layer is separated
  7. customchromatographed on silica gel
  8. washElution with 50% ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-5510325be0c54b6aaf7dd1a2e4f492b1
Source dataset
uspto-grants-1978_06
Patent number
US04096264

Reaction notes

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