Thiophenol → HCID 86644388, compound

HRID 1882343Notes

Reaction equation

HRID 1882343 reaction equation
[C:1]1([NH:7][C:8](=[O:25])[CH:9]=[C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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.C1(S)C=CC=CC=1.C(N(CC)CC)C>C(OCC)(=O)C>[C:1]1([NH:7][C:8](=[O:25])[CH2:9][CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 86644389HCID 86644389, compound

Product 1

HCID 86644388HCID 86644388, compoundYield 146.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N-phenyl-3,3-bis(phenylthio)acrylamide (2.04 g) were added thiophenol (8.21 mL) and triethylamine (1.12 mL), and the mixture was stirred at room temperature for 11 hours. To the reaction mixture was added ethyl acetate (50 mL), which was washed with a 1N aqueous sodium hydroxide solution, water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was isolated and purified by medium pressure preparative liquid chromatography (YAMAZEN SI-40C, hexane:ethyl acetate=85:15) to obtain N-phenyl-3,3-bis(phenylthio)propionamide (3.00 g) as an orange oil.

Workup

  1. washwas washed with a 1N aqueous sodium hydroxide solution, water
  2. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was isolated
  5. custompurified by medium pressure preparative liquid chromatography (YAMAZEN SI-40C, hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-f46da8ff825c4653a14499dc6f2d4a72
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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