BE513651A - - Google Patents
Info
- Publication number
- BE513651A BE513651A BE513651DA BE513651A BE 513651 A BE513651 A BE 513651A BE 513651D A BE513651D A BE 513651DA BE 513651 A BE513651 A BE 513651A
- Authority
- BE
- Belgium
- Prior art keywords
- dichloroacetamide
- nitrophenyl
- threo
- propanediol
- diol
- Prior art date
Links
- WCGGWVOVFQNRRS-UHFFFAOYSA-N Dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 15
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 13
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- WIIZWVCIJKGZOK-RKDXNWHRSA-N Chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 7
- 229960005091 Chloramphenicol Drugs 0.000 claims description 7
- ADOKXMIRQKPYNF-UHFFFAOYSA-N ClC(Cl)C(=O)NC(=O)C(Cl)Cl Chemical compound ClC(Cl)C(=O)NC(=O)C(Cl)Cl ADOKXMIRQKPYNF-UHFFFAOYSA-N 0.000 claims description 7
- ZSLOUCRTVABUPM-UHFFFAOYSA-N N-acetyl-2,2-dichloroacetamide Chemical compound CC(=O)NC(=O)C(Cl)Cl ZSLOUCRTVABUPM-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000003287 optical Effects 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AIWDDSHAFWUZBC-UHFFFAOYSA-N 2,2-dichloro-N-(1,3-dihydroxy-1-phenylpropan-2-yl)acetamide Chemical compound ClC(Cl)C(=O)NC(CO)C(O)C1=CC=CC=C1 AIWDDSHAFWUZBC-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- -1 amino diol Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000003115 biocidal Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- OCYJXSUPZMNXEN-UHFFFAOYSA-N 2-amino-1-(4-nitrophenyl)propane-1,3-diol Chemical compound OCC(N)C(O)C1=CC=C([N+]([O-])=O)C=C1 OCYJXSUPZMNXEN-UHFFFAOYSA-N 0.000 description 1
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 1
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 1
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 1
- WQNBHMVXZZJSSA-UHFFFAOYSA-N C(CC)(=O)NC(C(Cl)Cl)=O Chemical compound C(CC)(=O)NC(C(Cl)Cl)=O WQNBHMVXZZJSSA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KYRHYTFTZHTERI-UHFFFAOYSA-N ClC(C(=O)NC(C1=CC=C(C=C1)[N+](=O)[O-])=O)Cl Chemical compound ClC(C(=O)NC(C1=CC=C(C=C1)[N+](=O)[O-])=O)Cl KYRHYTFTZHTERI-UHFFFAOYSA-N 0.000 description 1
- PNQYSZDTKVZPTA-UHFFFAOYSA-N ClC(C(=O)NC(CCC)=O)Cl Chemical compound ClC(C(=O)NC(CCC)=O)Cl PNQYSZDTKVZPTA-UHFFFAOYSA-N 0.000 description 1
- AQYLOUAARCQMAS-UHFFFAOYSA-N ClC(C(=O)NC(COC)=O)Cl Chemical compound ClC(C(=O)NC(COC)=O)Cl AQYLOUAARCQMAS-UHFFFAOYSA-N 0.000 description 1
- 208000001786 Gonorrhea Diseases 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 1
- LRUVJUZYMYXNBL-UHFFFAOYSA-N N-(2,2-dichloroacetyl)benzamide Chemical compound ClC(Cl)C(=O)NC(=O)C1=CC=CC=C1 LRUVJUZYMYXNBL-UHFFFAOYSA-N 0.000 description 1
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 1
- 206010061393 Typhus Diseases 0.000 description 1
- 206010046577 Urinary tract infection Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940079866 intestinal antibiotics Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE513651A true BE513651A (zh) |
Family
ID=151712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE513651D BE513651A (zh) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE513651A (zh) |
-
0
- BE BE513651D patent/BE513651A/fr unknown
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