Pyridine → HCID 19438397, compound

HRID 260137Notes

Reaction equation

HRID 260137 reaction equation
[O-:1][C:2]#[N:3].[Na+].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([O:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([CH3:25])[C:20]=1[S:21](Cl)(=[O:23])=[O:22])=[O:15])[CH3:12]>C(#N)C>[OH-:1].[CH2:11]([O:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([CH3:25])[C:20]=1[S:21]([NH:3][C:2]([N+:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:1])(=[O:23])=[O:22])=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 517096Sodium CyanateHCID 109779631-methyl-4-ethoxycarbonylpyrazole-5-sulfonylchloride

Product 1

HCID 19438397HCID 19438397, compoundYield 158.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

1.08 g(16.6 mmole) of anhydrous sodium cyanate, 1.25 g(15.8 mmole) of dry pyridine and 20.0 g of dry acetonitrile were mixed together and the resulting mixture was then stirred under nitrogen atmosphere while maintaining the temperature of 40° C. To this mixture was added 3.80 g(15.0 mmole) of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonylchloride over one hour. The reaction mixture was then stirred for further 2 hours while maintaining the temperature of 40° to 45° C. to complete the reaction. After the reaction was completed, the reaction solution was filtered under nitrogen atmosphere. The solvent and the remaining pyridine were removed from the filtrate at normal temperature by means of a vacuum pump to obtain the crude product which was then washed with 10.00 g of dry ethyl ether and dried to obtain 4.68 g (Yield 92%) of the title compound as the white solid. ##STR13##

Workup

  1. stirringThe reaction mixture was then stirred for further 2 hours
  2. temperaturewhile maintaining the temperature of 40° to 45° C.
  3. customthe reaction
  4. filtrationthe reaction solution was filtered under nitrogen atmosphere
  5. customThe solvent and the remaining pyridine were removed from the filtrate at normal temperature by means of a vacuum pump
  6. customto obtain the crude product which
  7. washwas then washed with 10.00 g of dry ethyl ether
  8. customdried

Sources & evidence

ORD record
ord-c7e162e96689474bbd8c2c177452ac2e
Source dataset
uspto-grants-1996_06
Patent number
US05525730

Reaction notes

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