DE860067C - Verfahren zur Herstellung von Ketoacylaminoalkoholen - Google Patents
Verfahren zur Herstellung von KetoacylaminoalkoholenInfo
- Publication number
- DE860067C DE860067C DEP5178A DEP0005178A DE860067C DE 860067 C DE860067 C DE 860067C DE P5178 A DEP5178 A DE P5178A DE P0005178 A DEP0005178 A DE P0005178A DE 860067 C DE860067 C DE 860067C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- condensation
- ecm
- mixture
- formaldehyde
- 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 7
- 150000001298 alcohols Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- MIJZKZQWQXKSPA-UHFFFAOYSA-N n-phenacylbenzamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)C1=CC=CC=C1 MIJZKZQWQXKSPA-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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 |
|---|---|
| DE860067C true DE860067C (de) | 1952-12-18 |
Family
ID=21836248
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| DE1949P0005179 Expired DE860068C (de) | 1948-08-24 | 1949-10-25 | Herstellung von Aminodiolen |
| DEP98A Expired DE855264C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Acylaminodiolen |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP5177D Expired DE860066C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Ketoaminoalkoholderivaten |
| DE1949P0005179 Expired DE860068C (de) | 1948-08-24 | 1949-10-25 | Herstellung von Aminodiolen |
| DEP98A Expired DE855264C (de) | 1948-08-24 | 1949-10-25 | Verfahren zur Herstellung von Acylaminodiolen |
Country Status (6)
| Country | Link |
|---|---|
| CH (13) | CH285359A (enExample) |
| CY (1) | CY104A (enExample) |
| DE (4) | DE860067C (enExample) |
| FR (1) | FR980961A (enExample) |
| GB (4) | GB688109A (enExample) |
| NL (2) | NL67749C (enExample) |
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 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
- 1949-02-15 GB GB26696/51A patent/GB688107A/en not_active Expired
- 1949-02-15 GB GB2665/52A patent/GB688108A/en not_active Expired
- 1949-03-14 CH CH285359D patent/CH285359A/fr unknown
- 1949-03-14 CH CH285360D patent/CH285360A/fr unknown
- 1949-03-14 CH CH285137D patent/CH285137A/fr unknown
- 1949-03-14 CH CH285364D patent/CH285364A/fr unknown
- 1949-03-14 CH CH285361D patent/CH285361A/fr unknown
- 1949-03-14 CH CH285357D patent/CH285357A/fr unknown
- 1949-03-14 CH CH282087D patent/CH282087A/fr unknown
- 1949-03-14 CH CH285363D patent/CH285363A/fr unknown
- 1949-03-14 CH CH285362D patent/CH285362A/fr unknown
- 1949-03-14 CH CH285356D patent/CH285356A/fr unknown
- 1949-03-14 CH CH271929D patent/CH271929A/fr unknown
- 1949-03-14 CH CH285358D patent/CH285358A/fr unknown
- 1949-03-14 CH CH282086D patent/CH282086A/fr unknown
- 1949-10-25 DE DEP5178A patent/DE860067C/de not_active Expired
- 1949-10-25 DE DEP5177D patent/DE860066C/de not_active Expired
- 1949-10-25 DE DE1949P0005179 patent/DE860068C/de not_active Expired
- 1949-10-25 DE DEP98A patent/DE855264C/de not_active Expired
-
1953
- 1953-11-26 CY CY10556A patent/CY104A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL144893B (nl) | |
| NL67749C (enExample) | |
| CH285357A (fr) | 1952-08-31 |
| DE855264C (de) | 1952-11-10 |
| DE860066C (de) | 1952-12-18 |
| GB688108A (en) | 1953-02-25 |
| CH282086A (fr) | 1952-04-15 |
| DE860068C (de) | 1952-12-18 |
| CH285362A (fr) | 1952-08-31 |
| GB688107A (en) | 1953-02-25 |
| CH285364A (fr) | 1952-08-31 |
| CH285363A (fr) | 1952-08-31 |
| CH285356A (fr) | 1952-08-31 |
| CH285361A (fr) | 1952-08-31 |
| GB688023A (en) | 1953-02-25 |
| FR980961A (fr) | 1951-05-21 |
| GB688109A (en) | 1953-02-25 |
| CH271929A (fr) | 1950-11-30 |
| CH285359A (fr) | 1952-08-31 |
| CH282087A (fr) | 1952-04-15 |
| CY104A (en) | 1953-11-26 |
| CH285358A (fr) | 1952-08-31 |
| CH285137A (fr) | 1952-08-31 |
| CH285360A (fr) | 1952-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH507970A (de) | Verfahren zur Herstellung neuer desacylierter mehrkerniger Indole sowie deren Verwendung | |
| DE1159449B (de) | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren und deren Salzen | |
| CH628012A5 (de) | Verfahren zur herstellung von cyklopentenonderivaten. | |
| DE860067C (de) | Verfahren zur Herstellung von Ketoacylaminoalkoholen | |
| DE1695136C3 (de) | Verfahren zur Herstellung von 3-Amino-5-methylisoxazol | |
| DE2813340A1 (de) | Amidoxim-derivate, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1189997B (de) | Verfahren zur Herstellung von Butadiencarbonsaeurepiperaziden | |
| DE1445500A1 (de) | Verfahren zur Herstellung neuer Yohimban-Derivate und deren Salze | |
| DE942149C (de) | Verfahren zur Herstellung substituierter Glycinamide | |
| DE915214C (de) | Verfahren zur Umwandlung von Diazoketonen in ihre zugehoerigen Carbonsaeuren bzw. deren funktionellen Derivate | |
| CH416666A (de) | Verfahren zum Schützen der Aminogruppe | |
| DE890795C (de) | Verfahren zur Herstellung von Monoalkahverbindungen von Alkmdiolen | |
| DE1155119B (de) | Verfahren zur Herstellung von Derivaten von 2-Nitro-1-aminoaryl-N-sulfonsaeuren | |
| CH630616A5 (de) | Verfahren zur herstellung von 5-nitroso-2,4,6-triaminopyrimidin. | |
| DE930565C (de) | Verfahren zur Herstellung von 1-Phenyl-2-amino-1, 3-propandiolen oder von im Phenylrest substituierten 1-Phenyl-2-amino-1, 3-propandiolen | |
| DE897406C (de) | Verfahren zur Herstellung von Pyrazolonverbindungen | |
| DE1198371B (de) | Verfahren zur Herstellung N-haltiger Radikale | |
| DE893949C (de) | Verfahren zur Herstellung von aliphatischen Harnstoffderivaten | |
| DE962256C (de) | Verfahren zur Herstellung von Serinen aus Glykokoll und Aldehyden | |
| DE942811C (de) | Verfahren zur Herstellung von threo-1-p-Nitrophenyl-2-acylamidopropan-1,3-diolen | |
| AT202564B (de) | Verfahren zur Herstellung von neuen substituierten 3,4,6-Trioxohexahydropyridazinen | |
| DE962333C (de) | Verfahren zur Herstellung von Cyclohexanonoxim | |
| DE915938C (de) | Verfahren zur Herstellung von Oxoacylaminen der Cyclopentanopolyhydrophenanthrenreihe | |
| AT164031B (de) | Verfahren zur Herstellung von 2,4,6-Triaminophenyl-mono-äthern | |
| DE848043C (de) | Verfahren zur Herstellung von Formylverbindungen des 2,6-Dioxy-4,5-diaminopyrimidinsund seiner Methylderivate |