DE1257788B - Verfahren zur Herstellung von 5-Nitrofurfurylidenderivaten - Google Patents
Verfahren zur Herstellung von 5-NitrofurfurylidenderivatenInfo
- Publication number
- DE1257788B DE1257788B DEH46049A DEH0046049A DE1257788B DE 1257788 B DE1257788 B DE 1257788B DE H46049 A DEH46049 A DE H46049A DE H0046049 A DEH0046049 A DE H0046049A DE 1257788 B DE1257788 B DE 1257788B
- Authority
- DE
- Germany
- Prior art keywords
- nitrofurfurylidene
- carbohydrazide
- derivatives
- general formula
- radical
- 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
- -1 5-nitrofurfurylidene Chemical class 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 12
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- MMZMADORYMWYJD-UHFFFAOYSA-N 1-amino-3-[(5-nitrofuran-2-yl)methylideneamino]urea Chemical compound NNC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 MMZMADORYMWYJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WJYYUEQVECTILJ-UHFFFAOYSA-N 1,4-diiodo-2,5-dimethylbenzene Chemical compound CC1=CC(I)=C(C)C=C1I WJYYUEQVECTILJ-UHFFFAOYSA-N 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- LRRBMMMGCYHUNI-UHFFFAOYSA-N 4-nitrofuran-2-carbaldehyde Chemical compound [O-][N+](=O)C1=COC(C=O)=C1 LRRBMMMGCYHUNI-UHFFFAOYSA-N 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
- C07D307/75—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carboxylic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. hydrazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
- C07D307/76—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carbonic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. semicarbazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL1563361 | 1961-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1257788B true DE1257788B (de) | 1968-01-04 |
Family
ID=11043185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH46049A Pending DE1257788B (de) | 1961-06-15 | 1962-06-12 | Verfahren zur Herstellung von 5-Nitrofurfurylidenderivaten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3231570A (en, 2012) |
| BE (1) | BE618951A (en, 2012) |
| BR (1) | BR6240018D0 (en, 2012) |
| CH (1) | CH408050A (en, 2012) |
| DE (1) | DE1257788B (en, 2012) |
| DK (1) | DK105700C (en, 2012) |
| FR (1) | FR1352123A (en, 2012) |
| GB (1) | GB959130A (en, 2012) |
| NL (1) | NL279705A (en, 2012) |
| SE (1) | SE301323B (en, 2012) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416236A (en) * | 1945-08-28 | 1947-02-18 | Eaton Lab Inc | Series of nitrofuran compounds |
| US2416234A (en) * | 1945-08-28 | 1947-02-18 | Eaton Lab Inc | Series of nitrofuran compounds |
| US2726241A (en) * | 1954-01-15 | 1955-12-06 | Norwich Pharma Co | New series of nitrofurans |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB620888A (en) * | 1947-01-29 | 1949-03-31 | Eric Hoggarth | Furan derivatives |
| US3058988A (en) * | 1960-08-19 | 1962-10-16 | Abbott Lab | Carbohydrazides |
-
0
- NL NL279705D patent/NL279705A/xx unknown
- BE BE618951D patent/BE618951A/xx unknown
-
1962
- 1962-06-04 GB GB21398/62A patent/GB959130A/en not_active Expired
- 1962-06-06 US US200322A patent/US3231570A/en not_active Expired - Lifetime
- 1962-06-07 SE SE6396/62A patent/SE301323B/xx unknown
- 1962-06-12 DE DEH46049A patent/DE1257788B/de active Pending
- 1962-06-13 CH CH709762A patent/CH408050A/de unknown
- 1962-06-14 BR BR140018/62A patent/BR6240018D0/pt unknown
- 1962-06-14 DK DK263762AA patent/DK105700C/da active
- 1962-06-15 FR FR900891A patent/FR1352123A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416236A (en) * | 1945-08-28 | 1947-02-18 | Eaton Lab Inc | Series of nitrofuran compounds |
| US2416234A (en) * | 1945-08-28 | 1947-02-18 | Eaton Lab Inc | Series of nitrofuran compounds |
| US2726241A (en) * | 1954-01-15 | 1955-12-06 | Norwich Pharma Co | New series of nitrofurans |
Also Published As
| Publication number | Publication date |
|---|---|
| CH408050A (de) | 1966-02-28 |
| US3231570A (en) | 1966-01-25 |
| DK105700C (da) | 1966-10-31 |
| BE618951A (en, 2012) | |
| FR1352123A (fr) | 1964-02-14 |
| SE301323B (en, 2012) | 1968-06-04 |
| BR6240018D0 (pt) | 1973-05-24 |
| NL279705A (en, 2012) | |
| GB959130A (en) | 1964-05-27 |
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