Process for preparing 4-pentafluorosulfanylbenzoylguanidines

1. A compound of the formula XI

wherein:

R1 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, NR10R11, —O p —(CH 2 ) n —(CF 2 ) o —CF 3 or —(SO m ) q —(CH 2 ) r —(CF 2 ) s —CF 3 ;

R10 and R11 are, independently of one another, hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or —CH 2 —CF 3 ;

m is zero, 1 or 2;

n, o, p, q, r and s are, independently of one another, zero or 1;

R2 is hydrogen, F, Cl, Br, I, —(SO h ) z —(CH 2 ) k —(CF 2 ) l —CF 3 or alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms;

h is zero, 1 or 2;

z is zero or 1;

k is zero, 1, 2, 3 or 4;

l is zero or 1;

R3 and R4 are, independently of one another hydrogen or F;

R7 is CN,

and the salts thereof.

2. The compound of claim 1 wherein R1 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, methoxy, ethoxy, NR10R11, —O—CH 2 —CF 3 or —SO m —(CH 2 ) r —CF 3 , wherein R10 and R11 are independently of one another hydrogen, alkyl having 1, 2, 3or 4 carbon atoms or —CH 2 —CF 3 ; and where m is zero, 1 or 2 and r is zero or 1.

3. The compound of claim 2 wherein R1 is hydrogen or methyl.

4. The compound of claim 2 wherein R2 is hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3 or 4 carbon atoms or —SO h —(CH 2 ) k —CF 3 , wherein h is zero, 1 or 2 and k is zero or 1.

5. The compound of claim 4 wherein R2 is hydrogen.

6. The compound of claim 4 wherein R2 is selected from the group consisting of F, Cl, Br, and I.

7. The compound of claim 6 wherein R2 is Br.

8. A process for preparing a 4-acylguanidinophenyl-pentafluorosulfane comprising the steps of:

a) reacting a 4-aminophenyl-pentafluorosulfane with a halogenating agent under conditions effective to provide a 4-halophenyl-pentafluorosulfane;

b) reacting said 4-halophenyl-pentafluorosulfane with hydrogen cyanide or a salt thereof to provide a 4-nitrilephenyl-pentafluorosulfane;

c) hydrolyzing said 4-nitrilephenyl-pentafluorosulfane to provide a 4-carboxyphenyl-pentafluorosulfane; and

d) reacting said 4-carboxyphenyl-pentafluorosulfane with guanidine to provide said 4-acylguanidinophenyl-pentafluorosulfane.

9. A process according to claim 8 , wherein before step a), said method comprises the steps of:

reacting said 4-aminophenyl-pentafluorosulfane with a halogenating agent under conditions effective to prove a 2-halo-4-aminophenyl-pentafluorosulfane; and

reacting said 2-halo-4-aminophenyl-pentafluorosulfane with a nucleophile or organometallic compound effective to replace said 2-halo substituent with an R2 group, wherein:

R2 is —(SO h ) z —(CH 2 ) k —(CF 2 ) l —CF 3 , alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, in which 1, 2, 3 or 4 hydrogen atoms may be replaced by fluorine atoms;

h is zero, 1 or 2;

z is zero or 1;

k is zero, 1, 2, 3 or 4;

l is zero or 1;

or R2 is —(CH 2 ) t -phenyl or —O-phenyl, which are unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of —O u —(CH 2 ) v —CF 3 , alkoxy having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms and —SO 2 CH 3 ;

t is zero, 1, 2, 3 or 4;

u is zero or 1;

v is zero, 1, 2 or 3;

or R2 is —(CH 2 ) w -heteroaryl which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of —O x —(CH 2 ) y —CF 3 , alkoxy having 1, 2, 3 or 4 carbon atoms and alkyl having 1, 2, 3 or 4 carbon atoms, —SO 2 CH 3 ;

w is zero, 1, 2, 3 or 4;

x is zero or 1; and

y is zero, 1, 2 or 3.

10. The process of claim 8 wherein said 4-aminophenyl-pentafluorosulfane is formed by reacting a 4-nitrophenyl-sulfurpentafluoride with tin(II) chloride in a concentrated HCl solution.