Dimethylformamide → Methyl 3-cyano-2-methyl-6-(methylthio)benzoate

Temperature

150 °C

A mixture of methyl 3-iodo-2-methyl-6-methylsulphenylbenzoate (16.6 g) and cuprous cyanide (4.4 g) in dimethyl formamide (50 ml) was stirred and heated at 150° C. for 1 hour. The mixture was cooled to 90° C. and a solution of ferric chloride (18 g) in water (28 ml) and concentrated hydrochloric acid (5 ml) was added. The mixture was stirred and heated at 90° C. for 1 hour. The cooled mixture was filtered and the solid was washed with ether. The layers in the filtrate were separated and the aqueous layer was extracted with ether (100 ml). The combined organic layers were washed with water (2×100 ml), aqueous sodium sulphate solution (10%, 2×100 ml), water (2×100 ml), aqueous sodium hydroxide solution (2×100 ml), water (3×100 ml), dried (anhydrous MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 3-cyano-2-methyl-6-methylsulphenylbenzoate (10.0 g) as a brown oil NMR (CDCl3) 2.5(s,6H), 3.9(s,3H), 7.05(d,1H), 7.45(d,1H).

1. temperatureThe mixture was cooled to 90° C.
2. stirringThe mixture was stirred
3. temperatureheated at 90° C. for 1 hour
4. filtrationThe cooled mixture was filtered
5. washthe solid was washed with ether
6. customThe layers in the filtrate were separated
7. extractionthe aqueous layer was extracted with ether (100 ml)
8. washThe combined organic layers were washed with water (2×100 ml), aqueous sodium sulphate solution (10%, 2×100 ml), water (2×100 ml), aqueous sodium hydroxide solution (2×100 ml), water (3×100 ml)
9. dry with materialdried (anhydrous MgSO4)
10. filtrationfiltered
11. customThe filtrate was evaporated to dryness

ORD record

ord-d5b9d47c87e0433dac048cade12a837e

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05747424