Water → 2-Phenacylsulfanylacetonitrile

HRID 2396122Notes

Reaction equation

HRID 2396122 reaction equation
[SH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].Cl[CH2:12][C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH2:2]([S:1][CH2:12][C:13]#[N:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 110736092-Mercapto-1-phenylethanone

Product 1

HCID 3350192-Phenacylsulfanylacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part A. A mixture of 2-mercaptoacetophenone (6.96 g, 45.7 mmol), chloroacetonitrile (3.00 mL, 47.4 mmol), and potassium carbonate (7.21 g, 52.2 mmol) in tetrahydrofuran (100 mL) was stirred at ambient temperature for 12 hours. The mixture was poured into water (400 mL), and this was extracted with ethyl acetate (400 mL), then methylene chloride (400 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, phenacylthio-acetonitrile, as a pale pink oil (7.51 g, 39.3 mmol, 86%). 1H NMR (CDCl3): δ 7.96 (2H, dd, J=8.0, 1.1 Hz); 7.65-7.56(1H, m); 7.50 (2H, t, J=7.7 Hz); 4.13 (2H, s); 3.45 (2H, s). Mass spectrum (NH3 -CI/DDIP): m/z 210 (21%); 209 (100%); 192 (2%); 170 (1%); 139 (1%).

Workup

  1. extractionthis was extracted with ethyl acetate (400 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bd946bbe75f640f6a8f36f2f1196fd12
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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