GB517382A - Manufacture of iodinated esters - Google Patents

Manufacture of iodinated esters

Info

Publication number
GB517382A
GB517382A GB2209038A GB2209038A GB517382A GB 517382 A GB517382 A GB 517382A GB 2209038 A GB2209038 A GB 2209038A GB 2209038 A GB2209038 A GB 2209038A GB 517382 A GB517382 A GB 517382A
Authority
GB
United Kingdom
Prior art keywords
acid
condensed
iodo
octadecenol
alcohol
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
Application number
GB2209038A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2209038A priority Critical patent/GB517382A/en
Publication of GB517382A publication Critical patent/GB517382A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

517,382. Iodinated esters. BRANSCOMBE, D. J., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. July 25, 1938, No. 22090. [Class 2 (iii)] New iodinated esters are manufactured by causing a saturated or unsaturated aliphatic alcohol containing at least three carbon atoms to react with a mono- or poly-iodo aromatic or heterocyclic carboxylic acid or the acid halide thereof, or by causing a halogen ester of the alcohol to react with a neutral salt of the acid. When the reaction is between the acid and the alcohol, it is carried out in the presence of a dehydrating catalyst, e.g. hydrochloric acid or sulphuric acid. In each case the reaction is brought about by heating the reagents together, if desired in the presence of a solvent, for example benzene or xylene. Acids mentioned as starting materials are mono- and poly-iodo-benzoic acids, e.g. 2-iodobenzoic acid, 2:5 or 3:5-di-iodobenzoic acid, 2:3:5 or 3:4:5- tri-iodobenzoic acid and also acids containing substituents additional to the iodine atoms, for example amino, hydroxy or alkoxy groups and heterocyclic carboxylic acids such as mono- and di-iodohydroxypyridene carboxylic acids. Suitable alcohols and halogen esters mentioned are propanol, isopropanol, butanol, dodecanol, octadecanol, allyl alcohol and octadecenol and the corresponding chlorides or bromides. The products are useful as X-ray contrast agents for diagnostic purposes. In the examples (1) 2:5-di-iodobenzoyl chloride is condensed with octadecenol ; (2) 2:3:5-tri-iodobenzoyl chloride is condensed with (a) octadecenol and (b) dodecyl alcohol; (3) 2-iodobenzoyl chloride is condensed with allyl alcohol ; (4) 2:5-di-iodobenzoic acid is condensed with propanol; (5) 3:5-di-iodo-4-pyridone-N-acetic acid is condensed with (a) n-butanol, (b) isopropanol and (c) octadecenol, in the presence of sulphuric acid ; (6) 3:5-di-iodo-4-methoxyphenylacetic acid (prepared by diazotising 4-carboxymethyl- 2:6-di-iodoaniline, 'converting the diazo compound into the corresponding phenol and methylating this with dimethyl sulphate and alkali), is condensed with isopropanol in the presence of sulphuric acid ; (7) 3:5-di-iodo-4-aminophenyl-acetic acid (prepared by treating 4- aminophenyl-acetic acid with iodine and alkali or with iodine monochloride and hydrochloric acid) is condensed with isopropanol in the presence of sulphuric acid ; (8) 3:4:5-tri-iodophenacetyl chloride (made by treating diazotised 4-carboxymethyl-2:6-di-iodo-aniline with potassium iodate and heating the product with thioryl chloride) is condensed with octadecenol ; (9) silver 2:5-di-iodobenzoate is condensed with isopropylbromide and (10) silver tetra-io.dophthalic acid is condensed with (a) octadecenyl bromide and (b) dodecyl bromide.
GB2209038A 1938-07-25 1938-07-25 Manufacture of iodinated esters Expired GB517382A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2209038A GB517382A (en) 1938-07-25 1938-07-25 Manufacture of iodinated esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2209038A GB517382A (en) 1938-07-25 1938-07-25 Manufacture of iodinated esters

Publications (1)

Publication Number Publication Date
GB517382A true GB517382A (en) 1940-01-29

Family

ID=10173751

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2209038A Expired GB517382A (en) 1938-07-25 1938-07-25 Manufacture of iodinated esters

Country Status (1)

Country Link
GB (1) GB517382A (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2436270A (en) * 1944-05-22 1948-02-17 Schering Corp Polyiodo diaryl aliphatic acids and process for their manufacture
US2548852A (en) * 1949-01-29 1951-04-17 Sterling Drug Inc Alkoxyalkyl esters of iodo-alkoxy substituted phenyl acetic acids
US2571515A (en) * 1947-10-03 1951-10-16 Sterling Drug Inc Process of preparing iodinated amino benzoylamino alkanoic acids
US2572828A (en) * 1947-11-24 1951-10-30 Sterling Drug Inc Alkoxyalkyl esters of monoiodomono-alkoxybenzoic acids
US2580459A (en) * 1946-11-27 1952-01-01 Schering Corp Production of halogenated aryl fatty acids
US2606922A (en) * 1949-12-03 1952-08-12 Schering Corp Etherified phenyl aliphatic acids and their salts
US2612517A (en) * 1947-11-24 1952-09-30 Sterling Drug Inc Alkoxyalkyl iodobenzoates
US2705726A (en) * 1949-07-23 1955-04-05 Sterling Drug Inc Iodinated aminophenyl-carboxylic acids
US2790748A (en) * 1952-05-13 1957-04-30 Schering Corp Contrast agent
US2931830A (en) * 1952-03-20 1960-04-05 Sterling Drug Inc Beta-(2, 4, 6-triiodo-3-hydroxyphenyl)-propionic acids and preparation thereof
US2939881A (en) * 1957-03-20 1960-06-07 Mallinckrodt Chemical Works Iodo-benzoic acid derivatives
US2940996A (en) * 1960-06-14 M-hocbhxchzch
US2963474A (en) * 1958-07-23 1960-12-06 Mallinckrodt Chemical Works Organic compounds
US3021260A (en) * 1957-09-11 1962-02-13 Bayer Ag Mono-glycol esters of 3, 5-di-iodo-4-pyridone-nu-acetic acid X-ray contrast agentsin bronchography
US3133116A (en) * 1958-11-26 1964-05-12 Sterling Drug Inc Acylated 3-amino-5-hydroxy-2, 4, 6-triiodobenzoic acid and esters and salts thereof
US3218349A (en) * 1958-05-12 1965-11-16 Glaxo Lab Ltd Esters of tetraiodoanthranilic acid
US3361700A (en) * 1965-04-26 1968-01-02 Sterling Drug Inc Iodinated esters and resin compositions containing same
US3444192A (en) * 1961-04-17 1969-05-13 Hooker Chemical Corp Process for preparing alkoxychlorinated benzoic acids

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2940996A (en) * 1960-06-14 M-hocbhxchzch
US2436270A (en) * 1944-05-22 1948-02-17 Schering Corp Polyiodo diaryl aliphatic acids and process for their manufacture
US2580459A (en) * 1946-11-27 1952-01-01 Schering Corp Production of halogenated aryl fatty acids
US2571515A (en) * 1947-10-03 1951-10-16 Sterling Drug Inc Process of preparing iodinated amino benzoylamino alkanoic acids
US2572828A (en) * 1947-11-24 1951-10-30 Sterling Drug Inc Alkoxyalkyl esters of monoiodomono-alkoxybenzoic acids
US2612517A (en) * 1947-11-24 1952-09-30 Sterling Drug Inc Alkoxyalkyl iodobenzoates
US2548852A (en) * 1949-01-29 1951-04-17 Sterling Drug Inc Alkoxyalkyl esters of iodo-alkoxy substituted phenyl acetic acids
US2705726A (en) * 1949-07-23 1955-04-05 Sterling Drug Inc Iodinated aminophenyl-carboxylic acids
US2606922A (en) * 1949-12-03 1952-08-12 Schering Corp Etherified phenyl aliphatic acids and their salts
US2931830A (en) * 1952-03-20 1960-04-05 Sterling Drug Inc Beta-(2, 4, 6-triiodo-3-hydroxyphenyl)-propionic acids and preparation thereof
US2790748A (en) * 1952-05-13 1957-04-30 Schering Corp Contrast agent
US2939881A (en) * 1957-03-20 1960-06-07 Mallinckrodt Chemical Works Iodo-benzoic acid derivatives
US3021260A (en) * 1957-09-11 1962-02-13 Bayer Ag Mono-glycol esters of 3, 5-di-iodo-4-pyridone-nu-acetic acid X-ray contrast agentsin bronchography
US3218349A (en) * 1958-05-12 1965-11-16 Glaxo Lab Ltd Esters of tetraiodoanthranilic acid
US2963474A (en) * 1958-07-23 1960-12-06 Mallinckrodt Chemical Works Organic compounds
US3133116A (en) * 1958-11-26 1964-05-12 Sterling Drug Inc Acylated 3-amino-5-hydroxy-2, 4, 6-triiodobenzoic acid and esters and salts thereof
US3444192A (en) * 1961-04-17 1969-05-13 Hooker Chemical Corp Process for preparing alkoxychlorinated benzoic acids
US3361700A (en) * 1965-04-26 1968-01-02 Sterling Drug Inc Iodinated esters and resin compositions containing same

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