Iodine → 3-Pyridinecarbonitrile, 2,2'-dithiobis[4-methyl-6-phenyl-

HRID 436447Notes

Reaction equation

HRID 436447 reaction equation
[O-][CH2:2][CH3:3].[Na+].[Na].[C:6]([C:8]1[C:9]([SH:21])=[N:10][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][C:13]=1[CH3:14])#[N:7].II>C(O)C>[C:6]([C:8]1[C:9]([S:21][S:21][C:9]2[C:8]([C:6]#[N:7])=[C:13]([CH3:14])[CH:12]=[C:11]([C:3]3[CH:2]=[CH:20][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[N:10][C:11]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][C:13]=1[CH3:14])#[N:7]

Participants

6

Reactant 4

HCID 807IodineHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 178422625HCID 178422625, compound

Product 1

HCID 122699893-Pyridinecarbonitrile, 2,2'-dithiobis[4-methyl-6-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ethanolic solution containing sodium ethoxide was prepared by dissolving 0.74 g of metallic sodium in 70 ml of ethanol. To the solution was added 7.28 g of 3-cyano-4-methyl-6-phenyl-2-pyridinethiol. The mixture was stirred at room temperature for about 20 minutes to give a yellowish homogeneous solution. To this solution was added dropwise with stirring at room temperature 60 ml of ethanol containing 4.09 g of iodine. With addition, colorless crystals began to precipitate and there was obtained a suspension at the time of completion of the addition. After completion of the addition, stirring was continued for about 2 hours at room temperature. The reaction mixture was then filtered and the collected substance was dried to give 7.00 g of brownish crystals. The obtained crystals were recrystallized from benzene. The crystals recrystallized had a melting point of 200°~201° C and were identified by the elemental analyses and IR spectrum as bis(3-cyano-4-methyl-6-phenyl-2-pyridyl) disulfide.

Workup

  1. customwas prepared
  2. customto give a yellowish homogeneous solution
  3. additionTo this solution was added dropwise
  4. additionWith addition, colorless crystals
  5. customto precipitate
  6. customthere was obtained a suspension
  7. additionat the time of completion of the addition
  8. additionAfter completion of the addition
  9. stirringstirring
  10. waitwas continued for about 2 hours at room temperature
  11. filtrationThe reaction mixture was then filtered
  12. customthe collected substance was dried

Sources & evidence

ORD record
ord-c6b1bb488e054a8c813a829c98d20fb1
Source dataset
uspto-grants-1977_02
Patent number
US04009168

Reaction notes

Loading…