DE2138032A1 - N,n'-dihydroxy-benzimidazolidinone - Google Patents
N,n'-dihydroxy-benzimidazolidinoneInfo
- Publication number
- DE2138032A1 DE2138032A1 DE19712138032 DE2138032A DE2138032A1 DE 2138032 A1 DE2138032 A1 DE 2138032A1 DE 19712138032 DE19712138032 DE 19712138032 DE 2138032 A DE2138032 A DE 2138032A DE 2138032 A1 DE2138032 A1 DE 2138032A1
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- water
- lower alkyl
- dihydroxy
- hydroxides
- 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.)
- Pending
Links
- MVYNLSRYRQAPAX-UHFFFAOYSA-N 1,3-dihydroxybenzimidazol-2-one Chemical compound C1=CC=C2N(O)C(=O)N(O)C2=C1 MVYNLSRYRQAPAX-UHFFFAOYSA-N 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- -1 carbonamido Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE786841D BE786841A (fr) | 1971-07-29 | Nouvelles n,n'-dihydroxy benzimidazolodinones et leur procede de preparation | |
| DE19712138032 DE2138032A1 (de) | 1971-07-29 | 1971-07-29 | N,n'-dihydroxy-benzimidazolidinone |
| NL7210301A NL7210301A (enExample) | 1971-07-29 | 1972-07-26 | |
| GB3487872A GB1381056A (en) | 1971-07-29 | 1972-07-26 | N,n-dihydroxyimidazolinones |
| CH1121672A CH566999A5 (enExample) | 1971-07-29 | 1972-07-27 | |
| IT2751572A IT963445B (it) | 1971-07-29 | 1972-07-27 | N n di idrossibenzimidazolidinoni |
| JP7518672A JPS4930362A (enExample) | 1971-07-29 | 1972-07-28 | |
| FR7227424A FR2147753A5 (enExample) | 1971-07-29 | 1972-07-28 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712138032 DE2138032A1 (de) | 1971-07-29 | 1971-07-29 | N,n'-dihydroxy-benzimidazolidinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2138032A1 true DE2138032A1 (de) | 1973-02-08 |
Family
ID=5815226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712138032 Pending DE2138032A1 (de) | 1971-07-29 | 1971-07-29 | N,n'-dihydroxy-benzimidazolidinone |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4930362A (enExample) |
| BE (1) | BE786841A (enExample) |
| CH (1) | CH566999A5 (enExample) |
| DE (1) | DE2138032A1 (enExample) |
| FR (1) | FR2147753A5 (enExample) |
| GB (1) | GB1381056A (enExample) |
| IT (1) | IT963445B (enExample) |
| NL (1) | NL7210301A (enExample) |
-
0
- BE BE786841D patent/BE786841A/xx unknown
-
1971
- 1971-07-29 DE DE19712138032 patent/DE2138032A1/de active Pending
-
1972
- 1972-07-26 NL NL7210301A patent/NL7210301A/xx unknown
- 1972-07-26 GB GB3487872A patent/GB1381056A/en not_active Expired
- 1972-07-27 IT IT2751572A patent/IT963445B/it active
- 1972-07-27 CH CH1121672A patent/CH566999A5/xx not_active IP Right Cessation
- 1972-07-28 JP JP7518672A patent/JPS4930362A/ja active Pending
- 1972-07-28 FR FR7227424A patent/FR2147753A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH566999A5 (enExample) | 1975-09-30 |
| JPS4930362A (enExample) | 1974-03-18 |
| FR2147753A5 (enExample) | 1973-03-09 |
| NL7210301A (enExample) | 1973-01-31 |
| GB1381056A (en) | 1975-01-22 |
| IT963445B (it) | 1974-01-10 |
| BE786841A (fr) | 1973-01-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2855764A1 (de) | Verfahren zur herstellung von nitrodiarylamin unter verwendung eines promotors | |
| CH597199A5 (en) | 3-Phenyl pyridaz-6-ones prodn. | |
| DE2134518C3 (de) | Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe | |
| DE2627223C2 (enExample) | ||
| DE2138032A1 (de) | N,n'-dihydroxy-benzimidazolidinone | |
| DE1670248C3 (de) | Verfahren zur Herstellung von 4-Isothiazolcarbonsäuren | |
| DE2357063A1 (de) | Verfahren zur herstellung von 2,1,3- benzothiadiazin-4-on-2,2-dioxiden | |
| DE1147573B (de) | Verfahren zur Herstellung von Aminomethylenverbindungen | |
| DE2528697C2 (de) | Verfahren zur Herstellung von Salicylaldehyden | |
| DE1277244B (de) | Verfahren zur Herstellung von 2, 3-Dibrombuten-(2)-diol-(1,4),2,2,3,3-Tetrabrombutandiol-(1,4) und/oder Mucobromsaeure | |
| DE1933525A1 (de) | Verfahren zur Herstellung von chlor- und/oder cyansubstituierten Hydroxybenzonitrilen oder deren Alkali- oder Erdalkalisalzen | |
| DE2127898C3 (de) | Verfahren zur Herstellung von ge gebenenfalls inert substituierten o und p Aminothiophenolen | |
| DE2118493C3 (de) | Verfahren zur Herstellung von Aminostilbenen | |
| DE935129C (de) | Verfahren zur Herstellung von N-substituierten Sultamen | |
| DE660693C (de) | Verfahren zur Herstellung von in p-Stellung zum Stickstoffatom durch die Aldehydgruppe substituierten heterocyclischen Stickstoffverbindungen | |
| AT239243B (de) | Verfahren zur Herstellung von 2, 3-Dicyan-1, 4-dithia-anthrahydrochinon und -anthrachinon | |
| DE2706701A1 (de) | Verfahren zur herstellung von 3- chlor-5-halogenpyridazinen | |
| DE2163029C3 (de) | 4-Substituierte 1-Oxyd-6,7-methylendioxy-3-chinolincarbonsäurederivate | |
| DE1274121C2 (de) | Verfahren zur Herstellung von aromatischen Dithiocarbonsaeuren | |
| DE1670841C3 (de) | Verfahren zur Herstellung von 2-Styryl-benzotriazolen | |
| EP0041923A1 (de) | Verfahren zur Herstellung von N-(1'-Alkoxycarbonyläthyl)-2,6-dialkylanilinen | |
| AT367394B (de) | Verfahren zur herstellung neuer indanderivate | |
| AT259569B (de) | Verfahren zur Herstellung unsymmetrisch disubstituierter Harnstoffe | |
| DE171172C (enExample) | ||
| CH497437A (de) | Verfahren zur Herstellung von Benzotriazolen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |