Pyridine → HCID 20146254, compound

HRID 569744Notes

Reaction equation

HRID 569744 reaction equation
S(=NS(C)(=O)=O)=O.[S:8](=[N:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:14]([O:16][CH3:17])=[O:15])=O.N1C=CC=CC=1>C1C=CC=CC=1>[N:10]1[S:8][CH:21]=[C:20]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 10931522Methanesulfonamide, N-sulfinyl-HCID 20146257Methyl 3-sulphinylamino-4-methylbenzoate

Product 1

HCID 20146254HCID 20146254, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Conditions

Temperature
0 °C

Procedure

51.6 g (0.365 mole) of N-sulphinylmethanesulphonamide in 50 ml of benzene are added to a solution of 60 g (0.298 mole) of methyl 3-sulphinylamino-4-methylbenzoate in 200 ml of benzene at room temperature under argon. Thereafter, 24.9 g (0.315 mole) of pyridine, dissolved in 75 ml of benzene, are added in portions to the reaction mixture, while cooling with ice. The mixture is subsequently stirred at 0° C. for 10 minutes and then heated under reflux for 45 hours. After cooling, the benzene and pyridine are distilled off in vacuo, the oil which remains is poured into 150 ml of water and the mixture is acidified to pH 4 with 2N HCl. A brown solid thereby forms from the oil, and is extracted with chloroform. The chloroform extracts are washed with water, dried over MgSO4 and concentrated to dryness. The oil which remains crystallizes to a brown-yellow material by adding n-hexane, and the material is filtered off with suction and washed with n-hexane.

Workup

  1. additionare added in portions to the reaction mixture
  2. temperaturewhile cooling with ice
  3. temperatureheated
  4. temperatureunder reflux for 45 hours
  5. temperatureAfter cooling
  6. distillationthe benzene and pyridine are distilled off in vacuo
  7. additionthe oil which remains is poured into 150 ml of water
  8. extractionA brown solid thereby forms from the oil, and is extracted with chloroform
  9. washThe chloroform extracts are washed with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated to dryness
  12. customThe oil which remains crystallizes to a brown-yellow material
  13. additionby adding n-hexane
  14. filtrationthe material is filtered off with suction
  15. washwashed with n-hexane

Sources & evidence

ORD record
ord-b10e22ba1b024a4f94e667768c2f2260
Source dataset
uspto-grants-1988_03
Patent number
US04734407

Reaction notes

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