3-sulfanylbenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation I is followed starting from 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained. If the procedure described in Preparation I

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation I is followed starting from 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained. If the procedure described in Preparation I

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation I is followed starting from 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained. If the procedure described in Preparation I

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation I is followed starting from 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained. If the procedure described in Preparation I

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Mercaptobenzonitrile (0.40 g) and potassium carbonate (0.61 g) were suspended in N,N-dimethylformamide (5 mL). To the reaction mixture was added 4-bromobutyl acetate (0.63 g), and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5) to give the title compound (0.75 g). the resulting mixture was extracted with diethyl ether The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively dried over anhydrous magnesium sulfate The filtrate was concentrated under reduced pressure the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The required 3-Mercapto-benzonitrile is prepared from 3-Cyano-benzenesulfonyl chloride following the procedure for the preparation of 3-Mercaptobenzoic acid described in Journal of Heterocyclic Chemistry (1982), 19(4), 961-5.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.