Water → HCID 49758215, compound

HRID 2263289Notes

Reaction equation

HRID 2263289 reaction equation
[BrH:1].C(O)(=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:14](=O)[CH2:15][S:16][C:17]#[N:18])[CH:11]=[CH:12][CH:13]=1.O>C(O)(=O)C>[Br:1][C:17]1[S:16][CH:15]=[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=2)[N:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 58961414HCID 58961414, compound

Product 1

HCID 49758215HCID 49758215, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A 25% hydrogen bromide/acetic acid (65 ml) solution was added to a solution of 2-(3-methoxyphenyl)-2-oxoethyl thiocyanate (6.50 g, 31.4 mmol) in acetic acid (65 ml), and the mixture was stirred at 130° C. for 2 hours and at room temperature for 1 hour. Water was poured to the reaction mixture, 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 3.80 g (44.8%) of the desired product as a solid.

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-732ae61283b44bc9ac8bea25d60d64d8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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