Ethanol → HCID 59658535, compound

HRID 604963Notes

Reaction equation

HRID 604963 reaction equation
BrCC([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8])=O.[C:13]([O-:16])([O-])=O.[K+].[K+].[SH:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([OH:25])=[O:24].[CH2:29](O)C>>[C:7]([C:6]1[CH:5]=[C:12]([C:13](=[O:16])[CH2:29][S:19][C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23]([OH:25])=[O:24])[CH:11]=[CH:10][CH:9]=1)#[N:8]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 218465912-(Bromoacetyl)benzonitrile

Product 1

HCID 59658535HCID 59658535, compound

Procedure

Bromoacetylbenzonitrile (300 mg, 1.34 mmole) and anhydrous K2CO3 (740 mg, 5.35 mmole) in ethanol, 210 mg (1.36 mmole) 3-mercaptobenzoic acid was added and the mixture refluxed overnight. The solvent was evaporated and water added to the solid residue. The basic aqueous solution was extracted with ethyl acetate to remove unreacted -bromoacetylbenzonitrile. The aqueous layer was acidified and extracted with ethyl acetate, dried, evaporated and the residue purified by flash chromatography using chloroform followed by chloroform:methanol (99:1). Evaporation of high Rf yellow fractions resulted in a yellow powder (130 mg). M.S. m/s 296 (M−1)+. 1H NMR (DMSO) δ 4.31 (2H, s, —CH2-), 7.25-8.25 (8H, m, 8×ArH).

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThe solvent was evaporated
  3. additionwater added to the solid residue
  4. extractionThe basic aqueous solution was extracted with ethyl acetate
  5. customto remove unreacted -bromoacetylbenzonitrile
  6. extractionextracted with ethyl acetate
  7. customdried
  8. customevaporated
  9. customthe residue purified by flash chromatography
  10. customEvaporation of high Rf yellow fractions

Sources & evidence

ORD record
ord-0d8ecd51e6884688ad41d1b640e991b8
Source dataset
uspto-grants-2011_03
Patent number
US07910770B2

Reaction notes

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