GB2113679A - Method for making benzoylphenylureas - Google Patents
Method for making benzoylphenylureas Download PDFInfo
- Publication number
- GB2113679A GB2113679A GB08235280A GB8235280A GB2113679A GB 2113679 A GB2113679 A GB 2113679A GB 08235280 A GB08235280 A GB 08235280A GB 8235280 A GB8235280 A GB 8235280A GB 2113679 A GB2113679 A GB 2113679A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- substituted
- pyridyl
- alkylene
- halogenated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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Classifications
-
- 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
- C07C273/1809—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 with formation of the N-C(O)-N moiety
- C07C273/1818—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 with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing a compound having the general formula: <IMAGE> wherein X, Y, Z.R. R' and R'' are certain specified substituent groups which comprises reacting an aniline compound having the formula <IMAGE> with a halosubstituted alkylene or a compound of the formula R'' Hal in the presence of an alkali metal base, and thereafter without isolation of the reaction product so formed reacting with the appropriate benzoyl isocyanate after filtering any solids.
Description
SPECIFICATION
Method for 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, Cl, alkyl or haloalkyl; Z is O or S;Rand R' are individually H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; and R" is halogenated alkyl, halogenated alkylene, pyridyl or substituted pyridyl wherein the substituents are Cl, CFs or NO2, or phenyl or substituted phenyl which comprises reacting an aniline compound having the formula
wherein R, R' and Z are as above defined with a halo-substituted alkylene or with a compound of the formula
R"' wherein Hal is a halogen atom and R"' is halogenated alkyl, pyridyl or substituted pyridyl wherein the substituents are Cl, CF3 or NO2, or phenyl or substituted phenyl in the presence of an alkali metal base, and thereafter without isolation of the reaction product so-formed reacting with the appropriate benzoyl isocyanate after filtering any solids.
The reaction is a "one-pot" reaction and may be carried out at a temperature in the range of from -25" to 200"C. When the R" substituent is a halogenated alkane or halogenated alkylene, the reaction temperature is preferably from -25 C to +50 C. If other substituents are present, the reaction temperature is peferably from 25"C to 200"C.
A polar solvent such as, for example, sulpholane or acetone, or a mixture of sulpholane with methylene chloride is advantageously employed. Acetone is the most preferred solvent since it is cheap, it does not freeze under the conditions of the reaction and it is easily removed.
The preferred alkali metal base is sodium or potassium hydroxide.
Upon completion of the reaction, which may be determined by high pressure liquid chromatography (H PLC), the desired product may be separated from the reaction mixture by conventional means, for example, precipitation in water and filtration.
The invention is further illustrated by the following Examples.
EXAMPLE 1 N- (4- (2,2-Bichloro- 1, 1-difluoroethoxyphenyl)-amino)carbonyl-2-chlorobenzamide
A solution of 1,1-dichloro-2,2-difluoroethylene (22 g) in sulpholane and dichloromethane (85:15,20 ml) at 0 C as added dropwise over one hour to a stirred suspension of 4-aminophenol (13.7 g) and potassium hydroxide (5.04 g) in sulpholane and dichloromethane (85:15,60 ml) at OOC. The reaction was then stirred for 1.5 hours at 0 to 22"C and filtered through a bed of sodium sulphate/sulpholane.Xylene (15 ml) was added to the filtrate and the dichloromethane and xylene were removed from the reaction by distillation under reduced pressure; 2-Chlorobenzoylisocyanate (21.3 9) was added dropwise over one minute to the solution of 4-(2,2-dichloro-1,1-difluoroethoxy)aniline in sulpholane. The reaction mixture gave a brown mass on cooling which was allowed to stand overnight. The suspension was added to warm water (30"C, 2 liters) and stirred for five minutes, then filtered and the residue dried to give the desired compound as a brown solid (46.5 g, 95 percent pure).
EXAMPLE 2 N-4-(2,2-Dichloro- 1, 1-difluoroethoxyphenyl)-amino)carbonyl-2-chlorobenzamide.
1,1-Dichloro-2,2-difluoroethylene (40.6 g) at 0 C was added dropwise over 30 minutes to a stirred suspension of 4-aminophenol (27.4g) and potassium hydroxide (10.1 g) in acetone (220 ml) at 0 C. The reaction was stirred for a further 30 to 45 minutes at 0 to 22"C. The reaction mixture was then poured into xylene/water (200 ml of each). The organic layer was washed with water (50 ml) and then concentrated under reduced pressure until a solution of the aniline in xylene remained (156 g. 35.5% desired aniline, HPLC: equivalent to a yield of 91.1%).
The solution of 4-(2,2-dichloro-1,1 -difluoroethoxy) aniline in xylene was then reacted with 2chlorobenzoylisocyanate in the same manner as Example 1. The desired compound was obtained in a yield of above 80 percent.
As illustrated, the process of this invention provides a simple, convenient, "one-pot" procedure for making the desired benzoylphenylureas (aminocarbonylbenzamide).
Claims (9)
1. A process for preparing a compound having the general formula:
wherein X and Y are individualy H, F, Cl, alkyl or haloalkyl; Z is O or S; Rand R' are individually H, halogen alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; and R" is halogenated alkyl, halogenated alkylene, pyridyl or substituted pyridyl wherein the substituents are Cl, CF or NO2, or phenyl or substituted phenyl which comprises reacting an aniline compound having the formula
wherein R,R' and Z are as above defined with a halosubstitued alkylene our a compound or the formula R"Hal wherein Hal is a halogen atom and R"' is halogenated alkyl, pyridyl or substituted pyridyl wherein the substituents are Cl, CF3 or NO2, or phenyl or substituted phenyl in the presence of an alkali metal base, and thereafter without isolation of the reaction product so-formed reacting with the appropriate benozyl isocyanate after filtering any solids.
2. A process as claimed in claim 1 wherein R" is Cl, CF3 or NO2 substituted pyridyl or F, Cl, CF3, NO2 or CN substituted phenyl and the reaction temperature is from 25 to 200"C.
3. A process as claimed in claim 1 wherein R" is a halogenated alkane or halogenated alkylene and the reaction temperature is from -25" to +50"C.
4. A process as claimed in claim 3 wherein the aniline compound is p-aminophenol and the halosubstituted alkane is 1,1 -difluoro-1 ,2,3-trichloroethane.
5. A process as claimed in claim 3 wherein the aniline isp-aminophenol and the substituted alkylene is 1,1 -dichloro-2,2-difluoroethylene.
6. A process as claimed in any one of the preceding claims wherein the isocyanate is 2-chlorobenzoyl isocyanate.
7. A process as claimed in any one of the preceding claims wherein the reaction is carried out in acetone.
8. A process as claimed in claim 1 substantially as hereinbefore described with reference to Example 1 or
Example 2.
9. A benzoylphenyl urea as defined in claim 1 whenever prepared by a process as claimed in any one of the preceding claims.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08235280A GB2113679A (en) | 1981-12-22 | 1982-12-10 | Method for making benzoylphenylureas |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8138534 | 1981-12-22 | ||
| GB08235280A GB2113679A (en) | 1981-12-22 | 1982-12-10 | Method for making benzoylphenylureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2113679A true GB2113679A (en) | 1983-08-10 |
Family
ID=26281593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08235280A Withdrawn GB2113679A (en) | 1981-12-22 | 1982-12-10 | Method for making benzoylphenylureas |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2113679A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1982
- 1982-12-10 GB GB08235280A patent/GB2113679A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |