Potassium Carbonate → HCID 59658560, compound

HRID 2055921Notes

Reaction equation

HRID 2055921 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH2:21][CH3:22])[C:19]#[N:20]>C(O)C>[C:19]([CH2:18][CH2:21][CH2:22][S:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])#[N:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 131794392-Bromobutanenitrile

Product 1

HCID 59658560HCID 59658560, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To solution of 3-mercaptobenzoic acid (250 mg, 1.62 mmole) in ethanol (10 ml), anhydrous potassium carbonate (896 mg, 6.48 mmole) was added followed by bromobutyronitrile (239.97 mg, 1.62 mmole). The reaction mixture was refluxed overnight. The ethanol was evaporated and water added. The basic solution was extracted with ethyl acetate. The aqueous layer was acidified and the resulting precipitate filtered and dried to yield 196 mg product. M.S. m/s 220 (M−1)+. 1H NMR (DMSO) δ 1.79 (2H, m, —CH2-), 2.37 (2H, t, —CH2-), 3.02 (2H, t, CH2), 7.56 (1H, d, 1×ArH), 7.74 (1H, d, 1×ArH), 7.83 (1H, bs, 1H, 1×ArH).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe ethanol was evaporated
  3. additionwater added
  4. extractionThe basic solution was extracted with ethyl acetate
  5. filtrationthe resulting precipitate filtered
  6. customdried

Sources & evidence

ORD record
ord-50ca737ca56a4c40be08276c9ec11d41
Source dataset
uspto-grants-2008_02
Patent number
US07332631B2

Reaction notes

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