GB592461A - Process for the manufacture of n-substituted formylhippuric esters - Google Patents
Process for the manufacture of n-substituted formylhippuric estersInfo
- Publication number
- GB592461A GB592461A GB1150245A GB1150245A GB592461A GB 592461 A GB592461 A GB 592461A GB 1150245 A GB1150245 A GB 1150245A GB 1150245 A GB1150245 A GB 1150245A GB 592461 A GB592461 A GB 592461A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- alkyl
- ester
- ether
- treating
- 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
- 150000002148 esters Chemical class 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- 239000004471 Glycine Substances 0.000 abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl formate Chemical compound 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 230000000875 corresponding Effects 0.000 abstract 2
- NIDZUMSLERGAON-UHFFFAOYSA-N ethyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CCOC(=O)CNC NIDZUMSLERGAON-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- ULOLIZHBYWAICY-UHFFFAOYSA-N ethyl 2-(benzylamino)acetate Chemical compound CCOC(=O)CNCC1=CC=CC=C1 ULOLIZHBYWAICY-UHFFFAOYSA-N 0.000 abstract 1
- CLDAJCQRVCXYIR-UHFFFAOYSA-N ethyl 2-[acetyl(methyl)amino]acetate Chemical compound CCOC(=O)CN(C)C(C)=O CLDAJCQRVCXYIR-UHFFFAOYSA-N 0.000 abstract 1
- LFCSEQINKKXSDP-UHFFFAOYSA-N ethyl 2-[benzoyl(benzyl)amino]acetate Chemical compound C=1C=CC=CC=1C(=O)N(CC(=O)OCC)CC1=CC=CC=C1 LFCSEQINKKXSDP-UHFFFAOYSA-N 0.000 abstract 1
- CWLLFDLFVOLHIS-UHFFFAOYSA-N ethyl 2-[benzoyl(methyl)amino]acetate Chemical compound CCOC(=O)CN(C)C(=O)C1=CC=CC=C1 CWLLFDLFVOLHIS-UHFFFAOYSA-N 0.000 abstract 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001187 sodium carbonate Substances 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-Substituted a -formylglycine esters of the general formula <FORM:0592461/IV/1> or the tautomeric form <FORM:0592461/IV/2> wherein R and R1 represent alkyl or aralkyl radicals and R2 an alkyl or aryl radical, provided that when R1 is an alkyl radical R2 must be an aryl radical or a straight chain alkyl radical of 1-4 carbon atoms, are manufactured by treating an ester of the general formula R2CO.NR1.CH2.COOR with an alkyl formate in the presence of an alkali metal alkoxide, and acidifying the product. The reaction is conveniently effected in absolute alcohol, in a dry inert solvent such as ether or benzene, or in a mixture of alcohol and dry inert solvent. The esters used as starting materials may be made by treating an ethereal solution of the corresponding N-alkyl- or N-aralkyl-glycine ester with the appropriate acid chloride in the presence of an acid-binding substance, or by treating the hydrochloride of the N-alkyl- or N-aralkyl-glycine ester with the appropriate acid anhydride in the presence of the sodium salt of the corresponding acid. In examples: (1) sarcosine ethyl ester hydrochloride is treated in suspension in ether with benzoyl chloride in the presence of sodium carbonate, and the resulting ethyl N-methyl-hippurate is stirred with ethyl formate and a solution of potassium in alcohol and ether, yielding ethyl N-methyl-a -formylhippurate; (2) ethyl N-benzylhippurate is similarly prepared from ethyl benzylaminoacetate and is similarly converted to ethyl N - benzyl - a - formylhippuric ester; (3) sarcosine ethyl ester hydrochloride is warmed with acetic anhydride and sodium acetate, and the resulting N-acetylsarcosine ethyl ester is treated with ethyl formate as in (1) to produce a - formyl - N - acetylsarcosine ethyl ester; (4) the benzoyl chloride in (2) is replaced by caproyl chloride, yielding a -formyl-N-caproyl-N-benzylglycine ethyl ester. Sodium methoxide is also specified as a condensing agent.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB592461A true GB592461A (en) | 1947-09-18 |
Family
ID=1709445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1150245A Expired GB592461A (en) | 1945-05-05 | Process for the manufacture of n-substituted formylhippuric esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB592461A (en) |
-
1945
- 1945-05-05 GB GB1150245A patent/GB592461A/en not_active Expired
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