GB2106500A - Method for making benzoylphenylureas - Google Patents

Method for making benzoylphenylureas Download PDF

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GB2106500A
GB2106500A GB08128335A GB8128335A GB2106500A GB 2106500 A GB2106500 A GB 2106500A GB 08128335 A GB08128335 A GB 08128335A GB 8128335 A GB8128335 A GB 8128335A GB 2106500 A GB2106500 A GB 2106500A
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compound
halogenated
phenyl
percent
amino
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GB2106500B (en
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Robert Arthur Sewell
David Philip Clifford
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Dow Chemical Co Ltd
Dow Chemical Co
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Dow Chemical Co Ltd
Dow Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides

Abstract

A process for preparing a compound having the general formula: <IMAGE> wherein X and Y are individually H, F, Cl, alkyl or haloalkyl; Z is O or S; R and R' are individually H or Cl and R'' is alkyl aryl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl, comprises reacting a compound having the formula: <IMAGE> with a halogenated alkyl compound, a halogenated alkenyl compound, a halogenated alkylaryl compound, a halogenated pyridyl compound, or a halogenated phenyl compound, in the presence of an alkali metal base.

Description

SPECIFICATION Method of making benzoylphenylureas This invention relates to a method for making benzoylphenylureas and, more particularly, relates to a process for making a compound having the formula
wherein X and Y are individually H,F,CI, alkyl or haloalkyl; Z is O or S; R and R' are individually H or Cl and R" is alkyl aryl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl, which comprises reacting a compound having the formula:
with a halogenated alkyl compound, a halogenated alkenyl compound, a halogenated alkynyl compound, a halogenated alkylaryl compound, a halogenated pyridyl compound, or a halogenated phenyl compound in the presence of an alkali metal base.
The reaction may be carried out at a temperature in the range of from 250 to 1500C, but is preferably carried out at temperatures of from 0 to 25 0C. A polar solvent such as, for'example, sulpholane or acetone, or a mixture of sulpholane with methylene chloride is advantageously employed. The preferred alkali metal base is sodium or potassium hydroxide. Upon completion of the reaction, which may be determined by high pressure liquid chromatography (HPLC), the desired product may be separated from the reaction mixture by conventional means, for example, precipitation in water and filtration.
The benzoylphenylurea compounds used as starting materials in the process of the present invention may be prepared by the processes described in our co-pending patent applications No. 81 (Brit. Ref By3176) and 81 (Brit. Ref BA 3178) The invention is further illustrated by the following Examples.
Example 1 2-Chloro-N-(((4-(2,2-dichloro-1 ,1 -difluoro- ethoxy)phenyl)amino)carbonyl)benzamide To a stirred slurry of 2-chloro-N-(((4-hydroxyphenyl)amino)carbonyl) benzamide (1200 g) of potassium hydroxide (165 g) in sulpholane/dichloromethane (4.65 liters/0.52 liter) at00C was added 1,1-dichloro-2,2-difluoroethylene 826 g) in sulpholane/dichloromethane (0.93 liter/0.1 liter dropwise over an hour. The temperature was maintained throughout at below 100C. The reaction mixture was poured into water (40 liters), the precipitated product filtered, washed with water, and dried to give the desired compound as an off-white solid, 1.77 kg, 98 percent yield.
Example 2 2-Chloro-N-(((4(2,2-dichloro-1 1 -difluoro- ethoxy)phenyl)amino)carbonyl)benza mide To a stirred slurry of benzamide 2-chloro-N (((4-hydroxyphenyl)amino)carbonyl) (4.6 g) and potassium hydroxide (1.89 g) in acetone (50 ml) at 220C was added 1,1 -difluoro-1 2,2-trichloro- ethane (2.98 g). After complete conversion (HPLC, one hour), the reaction mixture was poured into water (1 liter) and the resulting suspension filtered, washed with water and dried to give the desired compound as a colorless solid.
(99 Percent yield by HPLC assay against an external standard). Repetition of this example, except for using 1.28 g of sodium hydroxide, resulted in an 86 percent yield of the desired product (HPLC assay).
Example 3 2-Chloro-N-(((4-(2,2-dibromo-1 -difluoro- ethoxy)phenyl)amino)carbonyl)benzamide To a stirred slurry of 2-chloro-N-(((4-hydroxyphenyl)amino)carbonyl)benzamide (4.6 g) and potassium hydroxide (1.64 g) in acetone (50 ml) at OOC was added 1,1 -dibromo-2,2-difluoroethylene (3.90 g). After complete conversion (HPLC, 30 minutes), the reaction mixture was poured into water (1 liter). The resulting suspension was filtered, washed with water and dried to give the desired compound, 6.6 g, 81 percent yield, m.p. 1 690 to 1 71 OC. Analysis (percent required/found): C, 37.49/37.71; H, 2.16/2.30; N, 5.47/5.54.
Example 4 2-Chloro-N-(((4-(2,4-dinitrophenoxy)phenyl)amino)carbonyl)benzamide To a stirred slurry of 2-chloro-N-(((4-hydroxyphenyl)amino)carbonyl)benzamide (4.6 g) and potassium hydroxide (0.65 g) in sulpholane (50 ml) at 220C was added 2,4-dinitro-fluorobenzene (2.98 g). A yellow precipitate rapidly formed. After complete reaction (HPLC, two hours), the mixture was poured into water (1 liter). The resulting suspension was filtered, washed with water and dried to give the desired compound as a yellow solid, 7.0 g, 96 percent, m.p. 2110 to 2140C. Analysis (percent required/found): C,52.57/52.55; H, 2.87/3.08; N,12.26/12.37.
Example 5 2-Chloro-N-(((4-(4-nitro-phenoxy)phenyl) amino)carbonyl)benzamide Procedure of Example 4 using 4-fluoro-nitrobenzene (2.26 g). The reaction was heated for eight hours at 600C. After filtering, the precipitated product was washed with methanol to remove unreacted starting material, yield 38 percent, m.p. 2180 to 2200C. Analysis (percent required/found): C, 58.32/58.38; H, 3.43/3.49; N, 10.20/10.13.
Example 6 2-chloro-N-( ( (4-(3-chloro-5-trifluoro methyi-2- pyridinyloxy)phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 2,3-dichloro 5-(trifluoromethyl)pyridine (3.42 g). The reaction was heated at 500 to 550C for six hours. After filtering the precipitated product was washed with methanol to removed unreacted starting material, yield 81 percent based on starting material consumed, m.p. 1960 to 19700.
Analysis (percent required/found): C, 51.06/51.11; H, 2.57/2.58; N, 8.93/8.87.
Example 7 2-Chlorn-N-(((4-(3,4,5,6-tetrachloropyridinyl- oxy)phenyl)amino)carbonyl)benzamide Procedure'of Example 4 using 2-fluoro tetrachloropyridine (3.76 g). The reaction was heated at 600C for 30 minutes. After filtering, the precipitated product was washed with methanol to remove unreacted starting material yield 50 percent, m.p. 2500 to 2530C. Analysis (percent required/found): C, 45.09/45.35; H, 1.99/2.20 N, 8.30/8.40.
Example 8 2-Chloro-N-(( (4-(2-fluoro-3,5,6-trichloro- pyridinyloxy)phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 2,4-difluorotrichloropyridine (3.5 g). The reaction was stirred for an hour at 300C. After filtering, the precipitated product was washed with methanol to remove unreacted starting material, yield 78 percent, m.p.
243' to 246 or. Analysis (percent required/found): C,46.62/46.57; H, 2.06/2.33; N, 8.59/7.93.
Example 9 2-Chloro-N-( ((4-(3,5-dichloro-6-fluoro-2- pyridinyloxy)phenyl)amino)carbonyl) benzamide Procedure of Example 4 using 3,5-dichloro2,6-difluoropyridine (4.6 g). The reaction was stirred for four hours. The precipitated product was washed with methanol to remove remaining starting material yield 63 percent, m.p. 2190 to 22100. Analysis (percent required/found): C, 50.1 7/50.1 4; H, 2.44/2.60; N, 9.24/9.1 8.
Example 10 2-Chloro-N-(((4-(l-phenylethoxy)phenyl)- amino)carbonyl)benzamide Procedure of Example 4 using phenethyl chloride (2.25 g) for 20 hours at 550C. After filtering, the precipitated product was washed with methanol to remove unreacted starting material, yield 25 percent based on starting material consumed, m.p. 1670 to 16900.
Analysis: (percent required/found): C, 66.90/66.95; H, 4.85/4.91; N, 7.09/7.05.
Example 11 2,6-Difluoro-N-(((4-(2,2-dibromo-1,1 -difluoro- ethoxy)phenyl)amino)carbonyl)benzamide To a stirred solution of 2,6-difluoro-N-(((4- hydroxyphenyl)amino)carbonyl)benzamide (1.0 g) and potassium hydroxide (0.2 g) in sulpholane (20 ml) at 220C was added 1,1-dibromo-2,2-dif 1,1-dibromo-2,2-difíuoro- ethylene (0.8 g). After 4 hours, the reaction mixture was poured into water (1 liter). The resulting suspension was filtered, washed with water and dried to give the desired compound, 1.1 g, 63 percent, m.p. 2080 to 210 C. Analysis (percent required/found): C, 37.38/37.53; H, 1.96/2.13; N, 5.45/5.51.
Example 12 2-Chloro-N-(((4-(2,3,5,6-tetrachloropyridinyl- oxy)phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 2,3,5,6-tetra chioro-4-methyl-sulphonyl pyridine (4.72 g). After filtering, the precipitated product was washed with methanol to give the desired compound as a colorless solid, 5.6 g, 69 percent, m.p. 2280 to 230 C. Analysis (percent required/found): C, 45.09/44.87; H, 1.99/1.99; N, 8.30/8.43.
Example 13 2-Chloro-N-(((4-(4-amino-3,5-dichloro-6fluoropyridinyloxy)phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 4-amino-3, 5- dichloro-2,6-difluoropyridine (3.18 g). The reaction was heated for eight hours at 60 C. After filtering, the precipitated product was washed with methanol to give the desired product as a colourless solid, 3.2 g, 43 percent, m.p. 2460 to 2480C. Analysis (percent required/found): C, 48.58/48.66; H, 2.57/2.69; N, 11.93/11.85.
Example 14 2,6-Difluorn-N-(((3,5-dichlorn-4(2,4-dinitrn- phenoxy)phenyl)amino)carbonyl)benzamide To a stirred solution of 2,6-difluoro-N-(((3,5-.
dichloro-4-hydroxyphenyl)amino)carbonyl) benzamide (0.2 g) and potassium hydroxide (0.02 g) in sulpholane (15 ml) at 600C was added 2,4dinitrofluorobenzene (0.1 g). After three hours, the reaction mixture was poured into water (1 liter). The resulting suspension was filtered, washed with water and dried to give the desired compound, 0.15 g, 50 percent, m.p. 2160 to 12800. Analysis present required/found): C, 45.54/45.64; H, 1.91/2.02; N, 10.62/10.50.
Example 15 2-Chloro-N-(((3,5-dichloro-4-(2,4-dinitrophenoxy)phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 2-chloro-N (((3S5-dichloro-4-hydroxyphenyl)amino)carbonyl)- benzamide (5.75 g). The reaction was stirred at 400C for 30 minutes. After filtering, the precipitated product was washed with methanol to give the desired product, 7.4 g, 88 percent, m.p. 2260 to 2280C. Analysis (percent required/found): C, 45.67/45.62; H, 2.11/2.17; N, 10.65/10.76.
Example 16 2-Chloro-N-IX (4(2,4-dinitrophenylthio)phenyl) amino)carbony)benzamide Procedure of Example 4 using 2-chloro-N-(((4mercaptophenyl)amino)carbonyl)benzamide (4.9).
The reaction was stirred at 300C for five minutes.
After filtering, the precipitated product was washed with methanol to give the desired compound as an intense yellow solid, 6.2 g, 82 percent, m.p. 2300 to 232 OC, Analysis (percent required/found): C, 50.79/50.67; H, 2.77/2.85; N, 11.85/11.92.
Example 17 2-Chloro-N-(((4-(((2,2-dimethyl-3-(2,2 dichloroethenyl)cyclopropyl)carbonyl)oxy)- phenyl)amino)carbonyl)benzamide Procedure of Example 4 using 3-(2,2,-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (3.6 g) (instead of 2,4-dinitro fluorobenzene). After filtering, the precipitated product was washed with methanol to give the desired compound as a colourless solid, 2.8 g, 37 percent. m.p. 2030 to 2050C. Analysis (percent required/found): C, 55.77/55.69; H, 4.04/3.96; N, 5.91/5.99.
Example 18 2-Chloro-N-(((4-(ethyl(carbonyldioxy)- phenyl)amino)carbonyl)benzamide Procedure of Example 4 using ethyl chloroformate (1.7 g). After filtering, the precipitated product was recrystallized from ethanol/water to give the desired compound as an off-white solid, 1.0 g, 17 percent, m.p. 1580 to 1 590C. Analysis (percent required/found): C, 56.28/56.45; H, 4.17/4.18: N, 7.72/7.90.
Example 19 N-(((4-(3-Chloro-5-trifluoromethyl-2pyridinyloxy)phenyl)amino)carbonyl)-2,6difluorobenzamide a a stirred solution of 2,6-difluoro-N-(((4- hydroxyphenyl)amino)carbonyl)benzamide (1.0 g) and potassium hydroxide (0.1 g) in sulpholane (20 ml) at 300C was added 2,3-dichloro-5-trifluoromethylpyridine (0.74 g). After three hours at 550C, the reaction mixture was poured into water (1 liter). After filtering, the precipitated product was washed with methanol to give the desired compound as an off-white solid, 0.1 g, 6 percent, m.p. 1950 to 1 970C. Analysis (percent required/found): C, 50.91/51.13; H 2.35/2.51; N, 8.91/8.84.
Example 20 2-Chloro-N-(((4-(3-chloro-5-trifluoromethyl)-2- pyridinylthio)phenyl)amino) carbonyl)benzamide Procedure of Example 4 using 2-chloro-N(((4mercaptophenyl)amino)carbonyl)benzamide (4.9 g). After filtering, the precipitated product was washed with methanol to give the desired product as a colourless solid, 4.83 g, 62 percent, m.p.
2180 to 2220C. Analysis (percent required/found): C, 49.38/49.45; H, 2.49/2.67; N, 8.64/8.52.

Claims (11)

Claims
1. A process for preparing a compound having the general formula:
wherein X and Y are individually H, F, Cl alkyl or haloalkyl; Z is O or S; R and R' are individually H or Cl and R" is alkyl aryl, halogenated alkyl, halogenated alkylene, pyridyl, substituted pyridyl, phenyl or substituted phenyl, which comprises reacting a compound having the formula:
with a halogenated alkyl compound, a halogenated alkenyl compound, a halogenated alkylaryl compound, a halogenated pyridyl compound, or a halogenated phenyl compound, in the presence of an alkali metal base.
2. A process as claimed in claim 1 wherein the haloalkylene is 1 , 1 -dichloro-2,2-difluoro- ethylene.
3. A process as claimed in claim 1 wherein the haloalkane is l,l-difluoro-l ,2,2-trichloroethane.
4. A process as claimed in any one of the preceding claims wherein the reaction is carried out in a polar solvent.
5. A process as claimed in claim 4 wherein the reaction is carried out at a temperature in the range of from 250 to 1 500C.
6. A process as claimed in claim 4 wherein the solvent is sulpholane.
7. A process as claimed in claim 6 wherein the sulpholane is used as a solvent in admixture with methylene chloride at a temperature below 250C.
8. A process as claimed in claim 4 wherein the solvent is acetone.
9. A process as claimed in any one of the preceding claims wherein the alkali metal base is sodium or potassium hydroxide.
10. A process as claimed in claim 1 substantially as hereinbefore described with reference to any one of the Examples.
11. A benzoylphenylurea whenever prepared by a process as claimed in any one of the preceding claims.
GB08128335A 1981-09-18 1981-09-18 Method for making benzoylphenylureas Expired GB2106500B (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0115210A1 (en) * 1982-12-30 1984-08-08 Union Carbide Corporation Pesticidal benzoyl ureas and process for their preparation
EP0116728A1 (en) * 1983-01-24 1984-08-29 Duphar International Research B.V Composition active against mites, whitefly and thrips, pharmaceutical composition, and new benzoylureau compounds
US4632938A (en) * 1984-02-27 1986-12-30 Takeda Chemical Industries, Ltd. Thiophenylureas, their production and use
EP0243790A1 (en) * 1986-04-18 1987-11-04 Hoechst Aktiengesellschaft N-phenyl(thio)ureas and their functional derivatives, processes for their production and their use as pesticides
EP0318882A2 (en) * 1987-12-04 1989-06-07 Hoechst Aktiengesellschaft (Thio)benzoyl ureas, functional derivatives, process for their preparation, compositions and pesticidal use
US7173031B2 (en) 2004-06-28 2007-02-06 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
US7432373B2 (en) 2004-06-28 2008-10-07 Bristol-Meyers Squibb Company Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors
US7439246B2 (en) 2004-06-28 2008-10-21 Bristol-Myers Squibb Company Fused heterocyclic kinase inhibitors
US7459562B2 (en) 2004-04-23 2008-12-02 Bristol-Myers Squibb Company Monocyclic heterocycles as kinase inhibitors
US7566784B2 (en) 2004-04-26 2009-07-28 Bristol-Myers Squibb Company Bicyclic heterocycles as kinase inhibitors

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0115210A1 (en) * 1982-12-30 1984-08-08 Union Carbide Corporation Pesticidal benzoyl ureas and process for their preparation
EP0116728A1 (en) * 1983-01-24 1984-08-29 Duphar International Research B.V Composition active against mites, whitefly and thrips, pharmaceutical composition, and new benzoylureau compounds
US4632938A (en) * 1984-02-27 1986-12-30 Takeda Chemical Industries, Ltd. Thiophenylureas, their production and use
EP0243790A1 (en) * 1986-04-18 1987-11-04 Hoechst Aktiengesellschaft N-phenyl(thio)ureas and their functional derivatives, processes for their production and their use as pesticides
EP0318882A2 (en) * 1987-12-04 1989-06-07 Hoechst Aktiengesellschaft (Thio)benzoyl ureas, functional derivatives, process for their preparation, compositions and pesticidal use
EP0318882A3 (en) * 1987-12-04 1990-11-14 Hoechst Aktiengesellschaft (thio)benzoyl ureas, functional derivatives, process for their preparation, compositions and pesticidal use
US7459562B2 (en) 2004-04-23 2008-12-02 Bristol-Myers Squibb Company Monocyclic heterocycles as kinase inhibitors
US7714138B2 (en) 2004-04-23 2010-05-11 Bristol-Myers Squibb Company Monocyclic heterocycles as kinase inhibitors
US7989477B2 (en) 2004-04-23 2011-08-02 Bristol-Myers Squibb Company Monocyclic heterocycles as kinase inhibitors
US7566784B2 (en) 2004-04-26 2009-07-28 Bristol-Myers Squibb Company Bicyclic heterocycles as kinase inhibitors
US7432373B2 (en) 2004-06-28 2008-10-07 Bristol-Meyers Squibb Company Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors
US7439246B2 (en) 2004-06-28 2008-10-21 Bristol-Myers Squibb Company Fused heterocyclic kinase inhibitors
US7173031B2 (en) 2004-06-28 2007-02-06 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors

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