IP Library Granted Patent US 6,864,385
Granted Patent B2
US 6,864,385 · App. 10/330,166 · Granted Mar 8, 2005

Process for the preparation of 4-haloalkylnicotinonitriles

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Quick Facts
Patent No.
US 6,864,385
App. No.
10/330,166
Granted
Mar 8, 2005
Kind
B2
Abstract

4-Haloalkylnicotinonitriles having the formula (I) which are suitable as intermediates in the preparation of pesticides, are obtained by: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one R F —C(O)—CH═CH—NH 2   (II) in a condensation reaction with a compound of the formula (III) to (VII), (R 1 Z)CH═CH—CN  (III) (R 1 Z) 2 CH—CH 2 —CN  (IV) Hal-CH═CH—CN  (V) Hal 2 CH—CH 2 CN  (VI) HC≡C—CN  (VII), to give a compound of the formula (VIII), (IX) and/or (X), R F —C(O)—CH═CH—NH—CH═CH—CN  (VIII) R F —C(O)—CH═CH—NH—CH(ZR 1 )—CH 2 —CN  (IX) R F —C(O)—CH═CH—NH—CH(Hal)—CH 2 —CN  (X), wherein R F is (C 1 -C 4 )-haloalkyl, R 1 is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR 1 or OCO; and (b) subjecting the reaction product to a ring closure reaction.

Claims (14)

1. A compound having the formula (VIII), (IX) or (X):

R F —C(O)—CH═CH—NH—CH═CH—CN  (VIII)

R F —C(O)—CH═CH—NH—CH(ZR 1 )—CH 2 —CN  (IX)

R F —C(O)—CH═CH—NH—CH(Hal)—CH 2 —CN  (X)

wherein:

R F is (C 1 -C 4 )-haloalkyl;

R 1 is an alkyl group;

Z is O, S or OCO and

Hal is Cl or Br.

2. A compound as claimed in claim 1 , wherein R F is CH 2 F, CFCl 2 , CF 2 Cl, CF 3 or C 2 F 5 .

3. A compound as claimed in claim 2 , wherein R F is CF 3 .

4. A compound as claimed in claim 1 , wherein Z is O or OCO.

5. A compound as claimed in claim 4 , wherein R 1 is (C 1 -C 4 )-alkyl.

6. A compound as claimed in claim 5 , wherein R 1 is methyl or ethyl.

Assignments (1)
MERGER Recorded Jan 16, 2008
From: AVENTIS CROPSCIENCE GMBH
To: BAYER CROPSCIENCE AG
Reel/Frame 020371/0093 →