Patent ID: 6342633
Filing Date: 2002-01-29
Classification: A01N,C07C,C07D,C07F

Abstract:
A process for preparing a thioamide of formula (I)(b) R2 is hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl, C(O)R6, OH C1-C4alkoxy, NH2 or C1-C4alkylamine; R6 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C3-C6cycloalkyl, C1-C4alkoxycarbonyl or phenyl which is unsubstituted or at most trisubstituted; and in which R3 and R4 independently of one another are hydrogen, cyano, C1-C4alkyl, halo-C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl, cyclopropylmethyl, C1-C4alkoxy, C2-C5alkoxyalkyl, C1-C4alkoxycarbonyl, C1-C4alkylthio, C2-C5alkylthioalkyl; a ring having not more than 15 ring carbon atoms which can be polymembered, and is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S, it being possible for this ring to be bonded via an aliphatic bridge having not more than 4 carbon atoms and/or via either CO, oxygen or sulfur; or in which R3 and R4 together with the shared carbon atom are a ring or a polymembered ring system having not more than 15 ring carbon atoms which is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S; the possible substituents of all these rings mentioned for R3 and R4, either individually or in combination, being selected from amongst C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C1-C4haloalkoxy, halogen, cyano, cyano-C1-C2alkyl, cyano-C1-C2alkoxy, OH, NO2, SCN, thiocyanomethyl, Si(CH3)3, NH2, NH(C1-C4alkyl), N(C1-C4alkyl)2, C1-C4alkoxymethyl, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkoximinomethyl, â€”CSNH2, â€”SH, C1-C4alkylthio, C1-C4alkylthiomethyl, C2-C4alkenyloxy, C2-C4alkynyloxy, C2-C4haloalkenyloxy, C1-C4alkylsulfinylmethyl, C1-C4alkylsulfonylmethyl, phenylsulfonylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C3-C6cycloalkyl; phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio; it being possible for the last-mentioned aromatic substituents to have not more than three further substituents in the phenyl ring which are selected from amongst halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, CN and NO2 and it being possible for two of the substituents, of which there are not more than 3, to form, together with the adjacent substituents, an aliphatic bridge which has not more than 5 members and which has 0-2 oxygen atoms and 0-1 carbonyl group and which can be not more than tetrasubstituted by halogen, C1-C4alkyl, C1-C4alkoxy and/or by a single phenyl group, â€ƒwhich comprises: A) treating a compound of the formula VIII â€ƒwith PS5 or Lawesson reagent, or B) adding hydrogen sulfide in the presence of a base to a nitrile of the formula III â€ƒor C) reacting III with bis(trimethylsilyl)sulfide and sodium methylate; the substituents Y, R2, R3 and R4 thereby having the meanings as given for formula (I)(b).