US2852451A - Electrolytic preparation of 3-amino-2-oxazolidones - Google Patents
Electrolytic preparation of 3-amino-2-oxazolidones Download PDFInfo
- Publication number
- US2852451A US2852451A US371173A US37117353A US2852451A US 2852451 A US2852451 A US 2852451A US 371173 A US371173 A US 371173A US 37117353 A US37117353 A US 37117353A US 2852451 A US2852451 A US 2852451A
- Authority
- US
- United States
- Prior art keywords
- amino
- oxazolidones
- oxazolidone
- nitro
- alkyl
- 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 - Lifetime
Links
- NIHYUMUIKWTKQE-UHFFFAOYSA-N 3-amino-1,3-oxazolidin-2-id-4-one Chemical class NN1[CH-]OCC1=O NIHYUMUIKWTKQE-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- CWTGJAWJHPAMMZ-UHFFFAOYSA-N 3-nitro-1,3-oxazolidin-2-id-4-one Chemical compound [N+](=O)([O-])N1[CH-]OCC1=O CWTGJAWJHPAMMZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KYCJNIUHWNJNCT-UHFFFAOYSA-N 3-Amino-2-oxazolidone Chemical compound NN1CCOC1=O KYCJNIUHWNJNCT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
Definitions
- lower alkyl and hydroxy (lower) alkyl R is a member of the group consisting of hydrogen
- R is a member of the group consisting. of hydrogen
- the various members of the new series of 3-amino- 2-oxazolidones can be prepared by the electrolytic reduction of the corresponding 3-nitro-2-oxazo1idone derivative.
- sulfuric acid is employed as the catholyte, lead as the anode, a mercury pool as the cathode, and a current density of 0.204 amp./cm. is used for one hour at a temperature of 5 to C.
- This reduction produces the desired 3-amino-2-oxazolidone derivative from the corresponding 3-nitro-2-oxazolidone.
- 3-nitro-2-oxazolidone is reduced electrolytically, using cc. of 10% sulfuric acid as the catholyte, a lead anode, a mercury pool cathode and a current density of 0.204 amp./cm. for one hour at a temperature of 5 10 C. At the end of this time the aqueous solution is separated from the mercury.
Description
United States Patent ELECTROLYTIC PREPARATION OXAZOLIDONES Gabriel Gever, Oxford, N. Y., assignor, by mesne assignments, to The Norwich Pharmacal Company, Norwich, N. Y a corporation of New York No Drawing. Original application February 28, 1952, Serial No. 274,067, now Patent No. 2,652,402, dated September 15, 1953. Divided and this application July 29, 1953, Serial No. 371,173
1 Claim. (Cl. 204-74) OF 3-AMINO-2- wherein R is a member of the alkyl and hydroxy (lower) alkyl R, is a member of the group consisting of hydrogen,
lower alkyl and hydroxy (lower) alkyl R is a member of the group consisting of hydrogen,
lower alkyl and hydroxy (lower) alkyl, and
R is a member of the group consisting. of hydrogen,
lower alkyl and hydroxy (lower) alkyl The new compounds of the series are particularly useful as intermediates for the preparation of members of a series of N-(5-nitro-2-furyl)alkylidene-3-amino-2- oxazolidones, notably, N-(5-nitro-2-furfurylidene)-3- amino-2-oxazo1idone, which I have invented and which form the subject of my co-pending application, Serial No. 274,066, filed February 28, 1952, now Patent No. 2,742,462. This application is a division of my co-pending application Serial No. 274,067, filed February 28, 1952, now Patent No. 2,652,402.
The various members of the new series of 3-amino- 2-oxazolidones can be prepared by the electrolytic reduction of the corresponding 3-nitro-2-oxazo1idone derivative. In this method, sulfuric acid is employed as the catholyte, lead as the anode, a mercury pool as the cathode, and a current density of 0.204 amp./cm. is used for one hour at a temperature of 5 to C. This reduction produces the desired 3-amino-2-oxazolidone derivative from the corresponding 3-nitro-2-oxazolidone.
In order that my invention may to those skilled in the art, the preparation of members of the new series compound 3-amino-4,4-dimethyl-2-oxazolidone, by the method which I have invented is described briefly:
EXAMPLE I 3-amino-2-oxazolidone HzN-N'- C: O
0 Tar-C group consisting of hydrogen, lower 2,852,451 Patented Sept. 16, 1958 ice.
3-nitro-2-oxazolidone is reduced electrolytically, using cc. of 10% sulfuric acid as the catholyte, a lead anode, a mercury pool cathode and a current density of 0.204 amp./cm. for one hour at a temperature of 5 10 C. At the end of this time the aqueous solution is separated from the mercury.
EXAMPLE II 3-amino-4,4-dimethyl-2-oxazolidone H2NNCO Cs CH3 a 3-amino-2-oxazolidone which comprises electrolytically reducing a 3-nitro-2- oxazolidone represented by the formula:
have the significance above 3-nitro-2-oxazo1idone in a wherein R, R R and R given, by suspending the catholyte of dilute sulfuric acid connected with a lead anode and a mercury pool cathode, and using a current of a density of about 0.204 amp/cm. at a temperature of about 5-10 C.
References Cited in the file of this patent UNITED STATES PATENTS
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US371173A US2852451A (en) | 1952-02-28 | 1953-07-29 | Electrolytic preparation of 3-amino-2-oxazolidones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US274067A US2652402A (en) | 1952-02-28 | 1952-02-28 | Series of new-3-amino-2-oxazolidones and the preparation thereof |
| US371173A US2852451A (en) | 1952-02-28 | 1953-07-29 | Electrolytic preparation of 3-amino-2-oxazolidones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2852451A true US2852451A (en) | 1958-09-16 |
Family
ID=26956583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US371173A Expired - Lifetime US2852451A (en) | 1952-02-28 | 1953-07-29 | Electrolytic preparation of 3-amino-2-oxazolidones |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2852451A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3267011A (en) * | 1962-02-05 | 1966-08-16 | Allied Chem | Monoalkylhydrazine synthesis |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1926837A (en) * | 1931-07-10 | 1933-09-12 | Martin E Cupery | Electrolytic reduction of organic nitro compounds |
| US2485982A (en) * | 1944-03-13 | 1949-10-25 | Commercial Solvents Corp | Electrolytic production of aminoalcohols |
| US2589635A (en) * | 1945-03-13 | 1952-03-18 | Polytechnic Inst Brooklyn | Electrochemical process |
| US2652402A (en) * | 1952-02-28 | 1953-09-15 | Eaton Lab Inc | Series of new-3-amino-2-oxazolidones and the preparation thereof |
-
1953
- 1953-07-29 US US371173A patent/US2852451A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1926837A (en) * | 1931-07-10 | 1933-09-12 | Martin E Cupery | Electrolytic reduction of organic nitro compounds |
| US2485982A (en) * | 1944-03-13 | 1949-10-25 | Commercial Solvents Corp | Electrolytic production of aminoalcohols |
| US2589635A (en) * | 1945-03-13 | 1952-03-18 | Polytechnic Inst Brooklyn | Electrochemical process |
| US2652402A (en) * | 1952-02-28 | 1953-09-15 | Eaton Lab Inc | Series of new-3-amino-2-oxazolidones and the preparation thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3267011A (en) * | 1962-02-05 | 1966-08-16 | Allied Chem | Monoalkylhydrazine synthesis |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ALLEN | The preparation of some substituted glycols by electrolytic reduction | |
| US2852451A (en) | Electrolytic preparation of 3-amino-2-oxazolidones | |
| GB1318291A (en) | Carboxamide derivatives and fungicidal compositions containing them | |
| GB1033777A (en) | Bis-anilide derivatives | |
| GB951107A (en) | Improvements relating to a-nor-steroid compounds | |
| ES400452A1 (en) | Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds | |
| SE7510785L (en) | WAY TO PRODUCE NEW, NITROGENIC, POLYCYCLIC ASSOCIATIONS | |
| CH389608A (en) | Process for the production of new ethers | |
| GB1070139A (en) | Novel imidazothiazole derivatives and a process for preparation thereof | |
| GB1087532A (en) | New isonitriles and biocidal preparations containing them | |
| US2748148A (en) | Substituted nu-carbamyl glycidamides | |
| DE2063502C3 (en) | Process for the preparation of aminocarboxylic acid precursors | |
| GB1372850A (en) | Acidic copper electrolytes | |
| GB1094810A (en) | Unsaturated 4,5-seco-steroid compounds, and processes for their preparation | |
| GB1043517A (en) | A process for the preparation of ª‡,ª‡-disubstituted succinimides, and the compounds thus prepared | |
| GB808187A (en) | Weedkilling compositions | |
| GB1085083A (en) | Improvements in or relating to benzimidazoles and the manufacture thereof | |
| GB1472368A (en) | Process for the preparation of 4-hydroxy-3-methoxy-phenylace tonitrile | |
| DE1063601B (en) | Process for the preparation of Schiff's bases from saturated N-heterocyclic compounds which have an amino group on the ring-shaped nitrogen atom, and nitro-acylthiophenes | |
| GB1049769A (en) | Organic compounds containing an isocyclic and a heterocyclic non-aromatic ring and aprocess for the production of these compounds | |
| ES275437A1 (en) | Amino-alkylidene-dibenzocycloheptene derivatives | |
| GB933430A (en) | Process for the prepaartion of group ó¾ metals of the periodic system | |
| GB988655A (en) | Androstan-3-one derivatives | |
| ES280753A1 (en) | Procedure for preparing penicilline (Machine-translation by Google Translate, not legally binding) | |
| GB885579A (en) | Imidazole quinones |