IE32031L - Nitrofuran derivatives - Google Patents
Nitrofuran derivativesInfo
- Publication number
- IE32031L IE32031L IE48268A IE48268A IE32031L IE 32031 L IE32031 L IE 32031L IE 48268 A IE48268 A IE 48268A IE 48268 A IE48268 A IE 48268A IE 32031 L IE32031 L IE 32031L
- Authority
- IE
- Ireland
- Prior art keywords
- solution
- ether
- added
- washed
- filtered
- Prior art date
Links
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 title abstract 2
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 239000002244 precipitate Substances 0.000 abstract 2
- HQDAJGNZGNZGCO-UHFFFAOYSA-N (propan-2-ylideneamino)urea Chemical compound CC(C)=NNC(N)=O HQDAJGNZGNZGCO-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- -1 N-methylaminoacetaldehyde diethylacetate Chemical compound 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Nitrofuran derivatives of the general formula (I). where R = hydrogen, methyl or hydroxymethyl. The compounds are antibacterial agents, having activity against a large number of gram negative and gram positive organisms. 147 g. N-methylaminoacetaldehyde diethylacetate was added to a solution of 115 g. acetone semicarbazone in 600 cc ethoxyethanol and the solution was refluxed for 6 hr. The solution was concentrated under reduced pressure and the residue diluted with ether. The precipitate formed was filtered off and washed with ether. The combined ether solution was concentrated under vacuum and 500 cc 10% sulphuric acid added to the residue. This solution was warmed on a steam bath and 113 g. 5-nitrofurfural dissolved in alcohol was added to the mixture which was then heated for 1 hr. on a steam bath. After cooling, the precipitate was filtered off, washed with water and dried to give 51 g. product, which was recrystallised from nitromethane to give pure 1-methyl-3-((5-nitrofurfurylidene)-amino) -4-imidazolinone-2. m.p. 238-240 deg.C.
[FR1605405A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65201567A | 1967-07-10 | 1967-07-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32031L true IE32031L (en) | 1969-01-10 |
| IE32031B1 IE32031B1 (en) | 1973-03-21 |
Family
ID=24615173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE48268A IE32031B1 (en) | 1967-07-10 | 1968-04-25 | 3-((5-nitrofurfurylidene)amino)-4-imidazolin-2-one |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT277986B (en) |
| BE (1) | BE717607A (en) |
| CH (1) | CH495375A (en) |
| DE (1) | DE1770806A1 (en) |
| DK (1) | DK115919B (en) |
| ES (1) | ES355759A1 (en) |
| FR (1) | FR1605405A (en) |
| GB (1) | GB1167471A (en) |
| IE (1) | IE32031B1 (en) |
| NL (1) | NL6809744A (en) |
-
1968
- 1968-04-08 DK DK156668A patent/DK115919B/en unknown
- 1968-04-23 GB GB1923568A patent/GB1167471A/en not_active Expired
- 1968-04-25 IE IE48268A patent/IE32031B1/en unknown
- 1968-07-04 ES ES355759A patent/ES355759A1/en not_active Expired
- 1968-07-04 BE BE717607D patent/BE717607A/xx unknown
- 1968-07-05 AT AT650568A patent/AT277986B/en not_active IP Right Cessation
- 1968-07-05 DE DE19681770806 patent/DE1770806A1/en active Pending
- 1968-07-05 CH CH1005268A patent/CH495375A/en not_active IP Right Cessation
- 1968-07-09 FR FR158484A patent/FR1605405A/en not_active Expired
- 1968-07-10 NL NL6809744A patent/NL6809744A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK115919B (en) | 1969-11-24 |
| CH495375A (en) | 1970-08-31 |
| IE32031B1 (en) | 1973-03-21 |
| FR1605405A (en) | 1975-04-18 |
| DE1770806A1 (en) | 1972-01-13 |
| ES355759A1 (en) | 1969-12-16 |
| AT277986B (en) | 1970-01-12 |
| BE717607A (en) | 1968-12-16 |
| GB1167471A (en) | 1969-10-15 |
| NL6809744A (en) | 1969-01-14 |
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