Potassium Carbonate → methyl N-cyano-N'-(2-nitrophenyl)sulfonylcarbamimidothioate

HRID 980511Notes

Reaction equation

HRID 980511 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:13])(=[O:12])=[O:11])([O-:3])=[O:2].[CH3:14][S:15][C:16](SC)=[N:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:18]([N:17]=[C:16]([S:15][CH3:14])[NH:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])#[N:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 1385102-Nitrobenzenesulfonamide

Product 1

HCID 178503935methyl N-cyano-N'-(2-nitrophenyl)sulfonylcarbamimidothioateYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.02 g (10.0 mmol) of 2-nitrobenzene-sulfonamide, 1.46 g (10.0 mmol) of dimethyl N-cyanodithioiminocarbonate and 1.38 g (10.0 mmol) of powdered, anhydrous K2CO3 in 16 ml of acetone was heated at reflux for 20 hours. The reaction mixture was filtered and the solid collected was washed several times with acetone. The filtrate was evaporated and the orange oily residue was triturated with ether to afford a solid. The solid was collected by filtration, washed with ether and suspended in 10 ml of 1N HCl. After stirring for 1 hour the solid was collected by filtration, washed with water and dried to yield 1.65 g (55 percent) of the desired product as a cream colored solid, mp 122° C. (decomposition). IR and 1H NMR spectra were consistent with the assigned structure.

Workup

  1. temperatureat reflux for 20 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe solid collected
  4. washwas washed several times with acetone
  5. customThe filtrate was evaporated
  6. customthe orange oily residue was triturated with ether
  7. customto afford a solid
  8. filtrationThe solid was collected by filtration
  9. washwashed with ether
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-115df81b68324205a17e422e6a9f6901
Source dataset
uspto-grants-1987_01
Patent number
US04638075

Reaction notes

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