DE855264C - Verfahren zur Herstellung von Acylaminodiolen - Google Patents
Verfahren zur Herstellung von AcylaminodiolenInfo
- Publication number
- DE855264C DE855264C DEP98A DEP0000098A DE855264C DE 855264 C DE855264 C DE 855264C DE P98 A DEP98 A DE P98A DE P0000098 A DEP0000098 A DE P0000098A DE 855264 C DE855264 C DE 855264C
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- nitro
- residue
- isopropanol
- acyl
- 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
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 40
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 10
- -1 aluminum alkoxide Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000004703 alkoxides Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000037386 Typhoid Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 201000008297 typhoid fever Diseases 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- KAOPWNFACLSZMA-UHFFFAOYSA-N ethyl acetate nitric acid Chemical class C(C)OC(C)=O.[N+](=O)(O)[O-] KAOPWNFACLSZMA-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US271929XA | 1948-08-24 | 1948-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE855264C true DE855264C (de) | 1952-11-10 |
Family
ID=21836248
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP98A Expired DE855264C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Acylaminodiolen |
| DE1949P0005179 Expired DE860068C (de) | 1948-08-24 | 1949-10-25 | Herstellung von Aminodiolen |
| DEP5178A Expired DE860067C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Ketoacylaminoalkoholen |
| DEP5177D Expired DE860066C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Ketoaminoalkoholderivaten |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1949P0005179 Expired DE860068C (de) | 1948-08-24 | 1949-10-25 | Herstellung von Aminodiolen |
| DEP5178A Expired DE860067C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Ketoacylaminoalkoholen |
| DEP5177D Expired DE860066C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Ketoaminoalkoholderivaten |
Country Status (6)
| Country | Link |
|---|---|
| CH (13) | CH282086A (forum.php) |
| CY (1) | CY104A (forum.php) |
| DE (4) | DE855264C (forum.php) |
| FR (1) | FR980961A (forum.php) |
| GB (4) | GB688107A (forum.php) |
| NL (2) | NL67749C (forum.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681364A (en) * | 1951-10-27 | 1954-06-15 | Parke Davis & Co | Process for the production of 1-p-nitrophenyl-2-acylamidopropane-1,3-diols |
-
0
- NL NL666608250A patent/NL144893B/xx unknown
- NL NL67749D patent/NL67749C/xx active
-
1949
- 1949-02-15 GB GB26696/51A patent/GB688107A/en not_active Expired
- 1949-02-15 GB GB2665/52A patent/GB688108A/en not_active Expired
- 1949-02-15 GB GB2666/52A patent/GB688109A/en not_active Expired
- 1949-02-15 GB GB4142/49A patent/GB688023A/en not_active Expired
- 1949-02-15 FR FR980961D patent/FR980961A/fr not_active Expired
- 1949-03-14 CH CH282086D patent/CH282086A/fr unknown
- 1949-03-14 CH CH285137D patent/CH285137A/fr unknown
- 1949-03-14 CH CH285357D patent/CH285357A/fr unknown
- 1949-03-14 CH CH282087D patent/CH282087A/fr unknown
- 1949-03-14 CH CH285362D patent/CH285362A/fr unknown
- 1949-03-14 CH CH285364D patent/CH285364A/fr unknown
- 1949-03-14 CH CH271929D patent/CH271929A/fr unknown
- 1949-03-14 CH CH285360D patent/CH285360A/fr unknown
- 1949-03-14 CH CH285358D patent/CH285358A/fr unknown
- 1949-03-14 CH CH285361D patent/CH285361A/fr unknown
- 1949-03-14 CH CH285363D patent/CH285363A/fr unknown
- 1949-03-14 CH CH285359D patent/CH285359A/fr unknown
- 1949-03-14 CH CH285356D patent/CH285356A/fr unknown
- 1949-10-25 DE DEP98A patent/DE855264C/de not_active Expired
- 1949-10-25 DE DE1949P0005179 patent/DE860068C/de not_active Expired
- 1949-10-25 DE DEP5178A patent/DE860067C/de not_active Expired
- 1949-10-25 DE DEP5177D patent/DE860066C/de not_active Expired
-
1953
- 1953-11-26 CY CY10556A patent/CY104A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH285357A (fr) | 1952-08-31 |
| DE860066C (de) | 1952-12-18 |
| NL144893B (nl) | |
| DE860068C (de) | 1952-12-18 |
| DE860067C (de) | 1952-12-18 |
| CH285356A (fr) | 1952-08-31 |
| CH285358A (fr) | 1952-08-31 |
| CH285137A (fr) | 1952-08-31 |
| CH285363A (fr) | 1952-08-31 |
| CH282086A (fr) | 1952-04-15 |
| CH285364A (fr) | 1952-08-31 |
| FR980961A (fr) | 1951-05-21 |
| GB688023A (en) | 1953-02-25 |
| CH282087A (fr) | 1952-04-15 |
| CH285361A (fr) | 1952-08-31 |
| CH285360A (fr) | 1952-08-31 |
| CH285362A (fr) | 1952-08-31 |
| GB688109A (en) | 1953-02-25 |
| GB688108A (en) | 1953-02-25 |
| NL67749C (forum.php) | |
| CH271929A (fr) | 1950-11-30 |
| GB688107A (en) | 1953-02-25 |
| CY104A (en) | 1953-11-26 |
| CH285359A (fr) | 1952-08-31 |
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