GB1194081A - Substituted Phenylphosphonamides and their Production - Google Patents
Substituted Phenylphosphonamides and their ProductionInfo
- Publication number
- GB1194081A GB1194081A GB453268A GB453268A GB1194081A GB 1194081 A GB1194081 A GB 1194081A GB 453268 A GB453268 A GB 453268A GB 453268 A GB453268 A GB 453268A GB 1194081 A GB1194081 A GB 1194081A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- prepared
- alkali metal
- compounds
- reacting
- 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.)
- Expired
Links
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 amino-phenyl Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000002828 nitro derivatives Chemical class 0.000 abstract 3
- FXNSXLYBUBJTOW-UHFFFAOYSA-N (2-nitrophenyl)phosphonamidic acid Chemical class NP(O)(=O)C1=CC=CC=C1[N+]([O-])=O FXNSXLYBUBJTOW-UHFFFAOYSA-N 0.000 abstract 2
- NRBGFVLLJKUKKQ-UHFFFAOYSA-N 2h-1,3,2-benzodiazaphosphole Chemical compound C1=CC=CC2=NPN=C21 NRBGFVLLJKUKKQ-UHFFFAOYSA-N 0.000 abstract 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 abstract 1
- AKUSZFPCJFNRSZ-UHFFFAOYSA-N 3,4-dimethyl-1,2-oxazole Chemical compound CC1=CON=C1C AKUSZFPCJFNRSZ-UHFFFAOYSA-N 0.000 abstract 1
- LSBIUXKNVUBKRI-UHFFFAOYSA-N 4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- MYGVXZUIDJDFCV-UHFFFAOYSA-N P(O)(O)=O.FC1=CC=CC(=C1)[N+](=O)[O-] Chemical compound P(O)(O)=O.FC1=CC=CC(=C1)[N+](=O)[O-] MYGVXZUIDJDFCV-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,194,081. Nuclearly - substituted phenylphosphonamides. MERCK & CO. Inc. 29 Jan., 1968 [31 Jan., 1967], No. 4532/68. Heading C2C. The invention comprises compounds of general formula in which R 1 and R 2 are H or halogen; R 3 is H and may also be F when both R 1 and R 2 are H; Q is -O- or -NH-; R 4 is H, C 1 -C 5 alkyl, substituted phenyl, phenyl, C 1 -C 5 aminoalkyl, amino-phenyl, or (heterocyclosulphamoyl)-phenyl or an alkali metal salt thereof; and Z is H, C 1 -C 5 alkyl, or (heterocyclosulphamoyl)-phenyl or alkali metal salt thereof, or QZ is an -O-(alkali metal) group, or the group -P(NHR 4 )(QZ) is 2-H- 1,3,2-benzodiazaphosphole. They are prepared by reduction of the corresponding nitrobenzenephosphonamides, e.g. by hydrogenation in the presence of a catalyst such as palladium, platinum oxide or Raney nickel. The invention also comprises the following processes for the preparation of nitrobenzenephosphonamides corresponding to the amino compounds of Formula (I); (a) nitro compounds in which QZ is also -NHR 4 are prepared by reacting the corresponding phosphonic dihalide with an amine, followed by treatment with water; (b) nitro compounds in which QZ is OM, M being an alkali metal, are prepared by reacting a compound produced by process (a) with one equivalent of aqueous alkali metal base of formula MOH; (c) nitro compounds in which R 4 is 2- amino phenyl and QZ is OR 5 , R 5 being C 1 -C 5 alkyl, are prepared by reacting a compound produced by process (a) in which the P(NHR 4 ) 2 group is 2-H-1,3,2-benzodiazaphosphole, wth an alkanol of formula R 5 OH. Specified heterocyclic rings when R 4 and Z are (heterocyclosulphamoyl)-phenyl are pyrimidine, methyl and dimethylpyrimidine, thiazole, oxazole, dimethylisoxazole and quinoxaline. The compounds have bactericidal properties. In Example XIV, 2-fluoro-4-nitrobenzenephosphonyl dichloride is prepared by reacting 2-fluoro-4-nitrobenzene phosphonic acid with PCl 5 .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61280067A | 1967-01-31 | 1967-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1194081A true GB1194081A (en) | 1970-06-10 |
Family
ID=24454709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB453268A Expired GB1194081A (en) | 1967-01-31 | 1968-01-29 | Substituted Phenylphosphonamides and their Production |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH507307A (en) |
| DE (1) | DE1668467A1 (en) |
| FR (1) | FR1573919A (en) |
| GB (1) | GB1194081A (en) |
| NL (1) | NL6800803A (en) |
-
1968
- 1968-01-18 NL NL6800803A patent/NL6800803A/xx unknown
- 1968-01-26 CH CH123768A patent/CH507307A/en not_active IP Right Cessation
- 1968-01-29 GB GB453268A patent/GB1194081A/en not_active Expired
- 1968-01-30 DE DE19681668467 patent/DE1668467A1/en active Pending
- 1968-01-31 FR FR1573919D patent/FR1573919A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6800803A (en) | 1968-08-01 |
| CH507307A (en) | 1971-05-15 |
| DE1668467A1 (en) | 1971-10-07 |
| FR1573919A (en) | 1969-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |