Sodium Chloride → HCID 25206561, compound

HRID 2061024Notes

Reaction equation

HRID 2061024 reaction equation
[C:1]1([N:7]=[C:8]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+].[Na+].[Cl-]>C1COCC1>[C:12]1([S:11][CH:10]([S:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][C:8]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7969ThiophenolHCID 23665647Potassium tert-butoxideHCID 67546115HCID 67546115, compound

Product 1

HCID 25206561HCID 25206561, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g of phenyl N-phenyl-3-(phenylthio)-2-propenimidothioate in THF (45 mL) was added 1.61 g of thiophenol and 88.9 g of potassium tert-butoxide at room temperature and stirred for 10 hours. To the reaction mixture was added 50 ml of a saturated NaCl solution and extracted with 100 ml of ethyl acetate. The organic layer was dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1 to hexane:ethyl acetate=10:1) to obtain 2.0 g of phenyl 3,3-bis(phenylthio)-N-phenylpropanimidothioate as a yellow oil.

Workup

  1. extractionextracted with 100 ml of ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1 to hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9b29443dab47452780a3f20ff370a205
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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