GB688023A - Improvements in and relating to the production of ketonic amino alcohol compounds - Google Patents
Improvements in and relating to the production of ketonic amino alcohol compoundsInfo
- Publication number
- GB688023A GB688023A GB4142/49A GB414249A GB688023A GB 688023 A GB688023 A GB 688023A GB 4142/49 A GB4142/49 A GB 4142/49A GB 414249 A GB414249 A GB 414249A GB 688023 A GB688023 A GB 688023A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- paraformaldehyde
- formaldehyde
- methanol
- sodium
- 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
- -1 amino alcohol compounds Chemical class 0.000 title abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 6
- 229920002866 paraformaldehyde Polymers 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 3
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 2
- 239000000920 calcium hydroxide Substances 0.000 abstract 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 abstract 1
- IYMVSNFKXCSUBE-UHFFFAOYSA-N 1-(2-amino-4-nitrophenyl)ethanone;hydrochloride Chemical compound Cl.CC(=O)C1=CC=C([N+]([O-])=O)C=C1N IYMVSNFKXCSUBE-UHFFFAOYSA-N 0.000 abstract 1
- GDJSHDDCLWALGA-UHFFFAOYSA-N 1-(2-bromo-4-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1Br GDJSHDDCLWALGA-UHFFFAOYSA-N 0.000 abstract 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- YXNAZGSJVAMGMB-UHFFFAOYSA-N N-(2-acetyl-5-nitrophenyl)-2,2-dichloroacetamide Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1)C(C)=O)NC(C(Cl)Cl)=O YXNAZGSJVAMGMB-UHFFFAOYSA-N 0.000 abstract 1
- QTBZCYFEMQJSMA-UHFFFAOYSA-N N-(2-acetyl-5-nitrophenyl)benzamide Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1)C(C)=O)NC(C1=CC=CC=C1)=O QTBZCYFEMQJSMA-UHFFFAOYSA-N 0.000 abstract 1
- YKEVEIFAPVPMDK-UHFFFAOYSA-N N-(6-acetyl-1-methyl-3-nitrocyclohexa-2,4-dien-1-yl)acetamide Chemical compound CC1(C(C=CC(=C1)[N+](=O)[O-])C(C)=O)NC(C)=O YKEVEIFAPVPMDK-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000011116 calcium hydroxide Nutrition 0.000 abstract 1
- 150000001983 dialkylethers Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- REEWHEDUSOBOSG-UHFFFAOYSA-N n-(2-acetyl-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1C(C)=O REEWHEDUSOBOSG-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 abstract 1
- 235000015497 potassium bicarbonate Nutrition 0.000 abstract 1
- 239000011736 potassium bicarbonate Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000011181 potassium carbonates Nutrition 0.000 abstract 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 235000015424 sodium Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 229940001593 sodium carbonate Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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 |
|---|---|
| GB688023A true GB688023A (en) | 1953-02-25 |
Family
ID=21836248
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2666/52A Expired GB688109A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of amino diols |
| GB2665/52A Expired GB688108A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of ª‡-acylamido-ª‰-acyloxypropiophenones |
| GB26696/51A Expired GB688107A (en) | 1948-08-24 | 1949-02-15 | Improvement in methods for obtaining p-nitro-ª‡-amino-ª‰-hydroxypropiophenones |
| GB4142/49A Expired GB688023A (en) | 1948-08-24 | 1949-02-15 | Improvements in and relating to the production of ketonic amino alcohol compounds |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2666/52A Expired GB688109A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of amino diols |
| GB2665/52A Expired GB688108A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of ª‡-acylamido-ª‰-acyloxypropiophenones |
| GB26696/51A Expired GB688107A (en) | 1948-08-24 | 1949-02-15 | Improvement in methods for obtaining p-nitro-ª‡-amino-ª‰-hydroxypropiophenones |
Country Status (6)
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 NL67749D patent/NL67749C/xx active
- NL NL666608250A patent/NL144893B/xx unknown
-
1949
- 1949-02-15 FR FR980961D patent/FR980961A/fr not_active Expired
- 1949-02-15 GB GB2666/52A patent/GB688109A/en not_active Expired
- 1949-02-15 GB GB2665/52A patent/GB688108A/en not_active Expired
- 1949-02-15 GB GB26696/51A patent/GB688107A/en not_active Expired
- 1949-02-15 GB GB4142/49A patent/GB688023A/en not_active Expired
- 1949-03-14 CH CH285358D patent/CH285358A/fr unknown
- 1949-03-14 CH CH285364D patent/CH285364A/fr unknown
- 1949-03-14 CH CH285361D patent/CH285361A/fr unknown
- 1949-03-14 CH CH285137D patent/CH285137A/fr unknown
- 1949-03-14 CH CH285360D patent/CH285360A/fr unknown
- 1949-03-14 CH CH285362D patent/CH285362A/fr unknown
- 1949-03-14 CH CH282087D patent/CH282087A/fr unknown
- 1949-03-14 CH CH285357D patent/CH285357A/fr unknown
- 1949-03-14 CH CH285359D patent/CH285359A/fr unknown
- 1949-03-14 CH CH285363D patent/CH285363A/fr unknown
- 1949-03-14 CH CH285356D patent/CH285356A/fr unknown
- 1949-03-14 CH CH271929D patent/CH271929A/fr unknown
- 1949-03-14 CH CH282086D patent/CH282086A/fr unknown
- 1949-10-25 DE DEP98A patent/DE855264C/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
- 1949-10-25 DE DE1949P0005179 patent/DE860068C/de not_active Expired
-
1953
- 1953-11-26 CY CY10556A patent/CY104A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH285364A (fr) | 1952-08-31 |
| CH285359A (fr) | 1952-08-31 |
| FR980961A (fr) | 1951-05-21 |
| CH285137A (fr) | 1952-08-31 |
| GB688107A (en) | 1953-02-25 |
| CY104A (en) | 1953-11-26 |
| CH285357A (fr) | 1952-08-31 |
| CH282086A (fr) | 1952-04-15 |
| DE855264C (de) | 1952-11-10 |
| CH282087A (fr) | 1952-04-15 |
| CH285362A (fr) | 1952-08-31 |
| DE860066C (de) | 1952-12-18 |
| CH285360A (fr) | 1952-08-31 |
| DE860067C (de) | 1952-12-18 |
| GB688108A (en) | 1953-02-25 |
| CH285361A (fr) | 1952-08-31 |
| GB688109A (en) | 1953-02-25 |
| NL144893B (nl) | |
| CH271929A (fr) | 1950-11-30 |
| CH285356A (fr) | 1952-08-31 |
| CH285358A (fr) | 1952-08-31 |
| DE860068C (de) | 1952-12-18 |
| NL67749C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| CH285363A (fr) | 1952-08-31 |
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