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

HRID 620660

反応式

HRID 620660 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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, anydrous 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 IN 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.

後処理

  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

出典と根拠

ORDレコード
ord-b05f2810c0d04135b12397dcfa6aa4d7
出典データセット
uspto-grants-1989_04
特許番号
US04822404

関連ノート

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