Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-06-24
1999-03-23
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568341, 568388, C07C 4554
Patent
active
058862315
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. National Stage Application of PCT/GB96/00082 filed Jan. 16, 1996 now WO 96/22958 published Aug. 1, 1996.
The present invention relates to the production of 2-(substituted benzoyl)-1,3-cyclohexanedione compounds.
2-(substituted benzoyl)-1,3-cyclohexanediones are known as herbicides from for example U.S. Pat. No. 4,780,127, U.S. Pat. No. 4,806,146, U.S. Pat. No. 4,946,981, U.S. Pat. No. 5,006,158, WO 9408988 and WO 9404524. One method of producing these compounds is by re-arrangement of an enol ester. This method is described in U.S. Pat. No. 4,780,127 and U.S. Pat. No. 4,695,673.
This process provides a means to obtain the desired compounds but generally employs organic bases such as triethylamine or employs polar aprotic solvents when alkali metal carbonates are used as base. The use of organic bases and polar aprotic solvents present problems on an industrial scale due to the need to recover these materials efficiently. It has surprisingly been found that non-polar solvents in combination with inorganic bases can be employed if a critical amount of water is added to the reaction medium.
According to the present invention there is provided a process for preparing a compound of formula (I) where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.7 is halogen, cyano, NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or RaS in which Ra is C.sub.1-4 alkyl; R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, CN, NO.sub.2, phenoxy or substituted phenoxy; R.sub.b S(O)n Om in which m is 0 or 1, n is 0, 1 or 2 and Rb is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, phenyl or benzyl, NHCOR.sub.c in which Rc is C.sub.1-4 alkyl, NRdRe in which Rd and Re independently are hydrogen or C.sub.1-4 alkyl; RfC(O)-- in which Rf is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or C.sub.1-4 alkoxy; SO.sub.2 NRgRh in which Rg and Rh independently are hydrogen or C.sub.1-4 alkyl; or any two of R.sup.8, R.sup.9 and R.sup.10 together with the carbon atoms to which they are attached form a 5 or 6 membered heterocyclic ring containing up to three heteroatoms selected from O, N or S and which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, .dbd.NOC.sub.1-4 alkyl or halogen; which process comprises the rearrangement of a compound of formula (II) where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in relation to formula (I), in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
As used herein the term "alkyl", refers to straight or branched chains. The term "haloalkyl" refers to an alkyl group substituted by at least one halogen. Similarly the term "haloalkoxy" refers to an alkoxy group substituted by at least one halogen. As used herein the term "halogen" refers to fluorine, chlorine, bromine and iodine.
Suitable optional substituents for phenoxy groups R.sup.8, R.sup.9 and R.sup.10 include halogen such as fluorine and chlorine and C.sub.1-4 haloalkyl.
A preferred group of compounds of formula (I) are those where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.7 is halogen, cyano, NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or RaS in which Ra is C.sub.1-4 alkyl; R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, CN, NO.sub.2, phenoxy or substituted phenoxy; R.sub.b S(O)n Om in which m is 0 or 1, n is 0, 1 or 2 and Rb is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, phenyl or benzyl, NHCOR.sub.c in which Rc is C.sub.1-4 alkyl, NRdRe in which Rd and Re independently are hydrogen or C.sub.1-4 alkyl; RfC(O)-- in which Rf is hydrogen, C.sub.1-4 alkyl, C.sub.1
REFERENCES:
patent: 4695673 (1987-09-01), Heather et al.
patent: 4780127 (1988-10-01), Michaely et al.
patent: 4806146 (1989-02-01), Carter
patent: 5468878 (1995-11-01), Nasuno et al.
patent: 5480858 (1996-01-01), Sakamoto et al.
Brown Stephen Martin
Rawlinson Howard
Geist Gary
Padmanabhan Sreeni
Thomson Marian T.
Zeneca Limited
LandOfFree
Process for the production of 2-(substituted benzoyl) 1,3 cycloh does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the production of 2-(substituted benzoyl) 1,3 cycloh, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of 2-(substituted benzoyl) 1,3 cycloh will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2127384