GB673639A - Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids - Google Patents
Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acidsInfo
- Publication number
- GB673639A GB673639A GB1784948A GB1784948A GB673639A GB 673639 A GB673639 A GB 673639A GB 1784948 A GB1784948 A GB 1784948A GB 1784948 A GB1784948 A GB 1784948A GB 673639 A GB673639 A GB 673639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- para
- acid
- chloride
- sodium
- added
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of a salt of a 4-benzoylamidosalicylic acid having the general formula <FORM:0673639/IV (b)/1> in which X is hydrogen or a halogen atom or a nitro or carboxylic acylamido group, which comprises treating para-amino-salicylic acid or a salt thereof with a benzoyl halide carrying the substituent X in the para position in the presence of an acid acceptor. In the preferred method the benzoyl halide, optionally dissolved in a solvent is added in portions to an aqueous solution of a water-soluble salt, such as an alkali metal salt of the para amino salicylic acid, the reaction mixture being maintained slightly alkaline by portionwise addition of alkali. The benzoyl halide and alkali may be added substantially simultaneously. Sodium and potassium salts of the para-aminosalicylic acid and sodium and potassium hydroxides as alkalies are preferred. Alternatively the para-aminosalicylic acid is dissolved in an organic base, e.g. pyridine, and the benzoyl halide is added to the solution with simultaneous or subsequent treatment with aqueous alkali to hydrolyse any o-acyl derivative formed. In either process the free acid may be liberated by acidification of the reaction mixture to a pH of about 3, preferably with a mineral acid. The acylating agent may be benzoyl chloride or bromide, para-nitrobenzoyl chloride, a parahalogen benzoyl chloride such as para-chlorobenzoyl chloride or an acylamidobenzoyl halide such as para-acetamidobenzoyl chloride. In examples (1) sodium hydroxide is added to an aqueous suspension of para-aminosalicylic acid to give a neutral solution. Acetone is added followed by nitrobenzoyl chloride in acetone and sodium hydroxide together. After stirring hydrochloric acid is added and the precipitated 4-(para-nitrobenzamido) salicylic acid is recrystallized from dilute alcohol; (2) 4-(para-chlorobenzamido) salicylic acid and the sodium salt are similarly prepared from sodium para-aminosalicylate dihydrate and para-chlorobenzoyl chloride; (3) 4-(para-acetamidobenzamido) salicylic acid and the sodium salt are prepared from paraacetamidobenzoyl chloride (prepared from p-acetamidobenzoic acid and thionyl chloride in dry ether) and sodium para-aminosalicylate dihydrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1784948A GB673639A (en) | 1948-07-02 | 1948-07-02 | Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1784948A GB673639A (en) | 1948-07-02 | 1948-07-02 | Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB673639A true GB673639A (en) | 1952-06-11 |
Family
ID=10102294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1784948A Expired GB673639A (en) | 1948-07-02 | 1948-07-02 | Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB673639A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969769B2 (en) | 2014-12-19 | 2018-05-15 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
| US10308677B2 (en) | 2014-12-19 | 2019-06-04 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
-
1948
- 1948-07-02 GB GB1784948A patent/GB673639A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969769B2 (en) | 2014-12-19 | 2018-05-15 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
| US10308677B2 (en) | 2014-12-19 | 2019-06-04 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
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