Ethanol → HCID 59658535, compound

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

Reactant 4

HCID 702Ethanol

HCID 11430Potassium Carbonate

HCID 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).