Chloroacetonitrile → 5-(Ethylsulfanyl)-3-hydroxythiophene-2-carbonitrile

192 g of ethyl α-carbethoxy-dithioacetate [Ber., Vol. 100 (1967), p. 1420] were added at 20° C. to a solution of 70 g of sodium methylate in one liter of methanol and after stirring for 5 minutes at 20° C., 76 g of chloroacetonitrile were added thereto. The mixture was stirred for 1 hour at 45° C. and 2 hours at 20° C. and after the addition of a solution of 70 g of sodium methylate in 500 ml of methanol, the mixture was stirred for 4 hours at 20° C. The mixture was evaporated to dryness under reduced pressure and the residue was dissolved in water. Toluene was added to the aqueous phase which was then acidified by addition of concentrated hydrochloric acid and the organic phase was rapidly separated by decanting. The organic phase was iced and vacuum filtered and the recovered crystals were dried to obtain 97 g of 2-cyano-3 -hydroxy-5-ethylthio-thiophene melting at 105° C. A microanalytically pure sample after crystallization from benzene melted at 105° C.

1. stirringThe mixture was stirred for 1 hour at 45° C. and 2 hours at 20° C.
2. stirringthe mixture was stirred for 4 hours at 20° C
3. customThe mixture was evaporated to dryness under reduced pressure
4. dissolutionthe residue was dissolved in water
5. additionToluene was added to the aqueous phase which
6. additionwas then acidified by addition of concentrated hydrochloric acid
7. customthe organic phase was rapidly separated
8. customby decanting
9. filtrationvacuum filtered
10. customthe recovered crystals were dried

ORDレコード

ord-a4bcfde11b1547fd965c4a8a2a282320

出典データセット

uspto-grants-1978_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04128562