Water → HCID 68778379, compound

HRID 2263197Notes

Reaction equation

HRID 2263197 reaction equation
[CH2:1]([CH:3]([S:12][C:13]#[N:14])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=C)[CH3:2].[BrH:15].C(O)(=O)C.O>C(O)(=O)C>[Br:15][C:13]1[S:12][C:3]([CH2:1][CH3:2])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 862451611-Ethyl-2-phenyl-2-propen-1-yl thiocyanate

Product 1

HCID 68778379HCID 68778379, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1-ethyl-2-phenylprop-2-en-1-yl thiocyanate (4.15 g, 20.2 mmol) in acetic acid (40 ml) was added a 25% hydrogen bromide/acetic acid (40 ml) solution, and the mixture was stirred at 130° C. for 2 hours. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (4.02 g, 74.2%) as an oil.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-c88dff46ed624628b4738a2a32025952
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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