CH429730A - Procédé de préparation de chlorhydrate d'amino-3-oxazolidone-2 - Google Patents
Procédé de préparation de chlorhydrate d'amino-3-oxazolidone-2Info
- Publication number
- CH429730A CH429730A CH766563A CH766563A CH429730A CH 429730 A CH429730 A CH 429730A CH 766563 A CH766563 A CH 766563A CH 766563 A CH766563 A CH 766563A CH 429730 A CH429730 A CH 429730A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxazolidone
- solution
- hydrochloride
- amino
- nitrosation
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims description 27
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 230000009935 nitrosation Effects 0.000 claims description 15
- 238000007034 nitrosation reaction Methods 0.000 claims description 15
- CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 235000010288 sodium nitrite Nutrition 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
- NZPARMKLAMASCC-UHFFFAOYSA-N 3-amino-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.NN1CCOC1=O NZPARMKLAMASCC-UHFFFAOYSA-N 0.000 claims description 5
- VWBXEIQLEMHSTF-UHFFFAOYSA-N 3-nitroso-1,3-oxazolidin-2-id-4-one Chemical compound O=NN1[CH-]OCC1=O VWBXEIQLEMHSTF-UHFFFAOYSA-N 0.000 claims description 5
- IVEXWRHLJIZLHF-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1-nitrosourea Chemical compound NC(=O)N(N=O)CCO IVEXWRHLJIZLHF-UHFFFAOYSA-N 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 nitro-5-furylidene Chemical group 0.000 description 3
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- YZOZVRSILRPWJC-UHFFFAOYSA-N 3-amino-1,3-oxazolidin-2-id-4-one;hydrochloride Chemical compound Cl.NN1[CH-]OCC1=O YZOZVRSILRPWJC-UHFFFAOYSA-N 0.000 description 1
- RJIPASZIRLEOEO-UHFFFAOYSA-N 3-nitroso-1,3-oxazolidine Chemical compound O=NN1CCOC1 RJIPASZIRLEOEO-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ISPQWZWLKSNQCG-UHFFFAOYSA-O [NH3+]C1O[C-]=NC1=O Chemical compound [NH3+]C1O[C-]=NC1=O ISPQWZWLKSNQCG-UHFFFAOYSA-O 0.000 description 1
- LPYIXHHGKPBPCF-UHFFFAOYSA-N acetic acid;5-nitrofuran-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)O1 LPYIXHHGKPBPCF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR901448A FR1346269A (fr) | 1962-06-21 | 1962-06-21 | Procédé de préparation de chlorhydrate d'amino-3 oxazolidone-2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH429730A true CH429730A (fr) | 1967-02-15 |
Family
ID=8781514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH766563A CH429730A (fr) | 1962-06-21 | 1963-06-20 | Procédé de préparation de chlorhydrate d'amino-3-oxazolidone-2 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT248427B (is") |
| BE (1) | BE633841A (is") |
| CH (1) | CH429730A (is") |
| DK (1) | DK103512C (is") |
| ES (1) | ES289063A1 (is") |
| FI (1) | FI40290B (is") |
| FR (1) | FR1346269A (is") |
| GB (1) | GB995475A (is") |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69230563T2 (de) * | 1991-08-14 | 2000-09-14 | Procter & Gamble Pharmaceuticals, Inc. | Oxazolidinon-derivate mit antiarrhythmischer und antifibrillatorische wirkung |
| US7977447B2 (en) | 2008-11-18 | 2011-07-12 | Sabic Innovative Plastics Ip B.V. | Method for making carbonates and esters |
-
0
- BE BE633841D patent/BE633841A/xx unknown
-
1962
- 1962-06-21 FR FR901448A patent/FR1346269A/fr not_active Expired
-
1963
- 1963-06-15 ES ES0289063A patent/ES289063A1/es not_active Expired
- 1963-06-18 DK DK287463A patent/DK103512C/da active
- 1963-06-20 GB GB2455363A patent/GB995475A/en not_active Expired
- 1963-06-20 FI FI125863A patent/FI40290B/fi not_active Application Discontinuation
- 1963-06-20 CH CH766563A patent/CH429730A/fr unknown
- 1963-06-21 AT AT501663A patent/AT248427B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| FR1346269A (fr) | 1963-12-20 |
| AT248427B (de) | 1966-07-25 |
| GB995475A (en) | 1965-06-16 |
| FI40290B (is") | 1968-09-02 |
| ES289063A1 (es) | 1963-11-01 |
| BE633841A (is") | |
| DK103512C (da) | 1966-01-17 |
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