GB643089A - Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers - Google Patents

Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers

Info

Publication number
GB643089A
GB643089A GB28381/47A GB2838147A GB643089A GB 643089 A GB643089 A GB 643089A GB 28381/47 A GB28381/47 A GB 28381/47A GB 2838147 A GB2838147 A GB 2838147A GB 643089 A GB643089 A GB 643089A
Authority
GB
United Kingdom
Prior art keywords
diiodo
methoxyphenoxy
nitrite
prepared
group
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
GB28381/47A
Inventor
Edward Teggin Borrows
John Charles Clayton
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB28381/47A priority Critical patent/GB643089A/en
Priority to FR989971D priority patent/FR989971A/en
Publication of GB643089A publication Critical patent/GB643089A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms

Landscapes

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

Abstract

2 : 6 - Dihalogenodiphenyl ethers of the formula <FORM:0643089/IV (b)/1> where X is chlorine, bromine or iodine, and R and R1 are as defined below, are prepared by the treatment of the corresponding diaminodiphenyl ether in glacial acetic acid and/or syrupy phosphoric acid with concentrated sulphuric acid and a suitable nitrite, and then the decomposition of the resultant tetrazo compound with a suitable halide in aqueous solution. R is alkyl, carbalkoxy, <FORM:0643089/IV (b)/2> where Z is alkyl group containing not more than four carbon atoms and Y is a group normally used to protect an amino group, e.g. acetyl or benzoyl; in addition, when R is the alanine type of side chain (-CH2.CH(NHY).COOZ), the compounds may possess optical activity. R1 is a hydroxyl group, a hydroxyl group protected by etherification or esterification, e.g. methoxyl, or an amino group protected by an acyl group. By a suitable nitrite is meant an inorganic nitrite, e.g. sodium, or an organic nitrite derived from an aliphatic alcohol of less than six carbon atoms, e.g. amyl nitrite, whilst a suitable halide means cuprous or an alkali metal, chloride, bromide or idodide. In the examples, (1), (2), 3 : 5-dinitro-4-(41-methoxyphenoxy)-benzyl hydantoin is hydrogenated to the diamino compound, tetrazotised, and treated with aqueous potassium iodide to give 3 : 5 - diiodo - 4 - (41 - methoxyphenoxy)-benzyl hydantoin, the following are also prepared in a similar manner from the appropriate dinitro compounds: 3 : 5-diiodo-4 - (41 - hydroxyphenoxy) - benzyl hydantoin 3 : 5 - dichloro - and 3 : 5 - dibromo - 4 - (41-methoxyphenoxy) - benzyl hydantoin, methyl 3 : 5 - diiodo - 4 - (41 - methoxyphenoxy)-benzoate, 3 : 5 - diiodo - 4 - (41 - methoxyphenoxy) - toluene, and l - 3 : 5 - diiodo - 4-(41 - methoxyphenoxy) - n - acetylphenylalamine ethyl ester. The 2 : 6-diaminodiphenyl ethers of the process are prepared by reduction of the 2 : 6-dinitro compounds, e.g. by hydrogenation, or with tin and hydrochloric acid. Samples have been furnished under Sect. 2(5) of the Acts of dl-5-(31 : 51-diiodo-41-p-acetamidophenoxybenzyl) hydantoin, 3 : 5 - diiodo - 4 - p-acetamidophenoxy - n - acetyl - dl - phenylalamine ethyl ester, and 3 : 5-diiodo-4-p-benzoylamidophenoxybenzoic acid methyl ester; all three are prepared as above from the appropriate 3 : 5-dinitro compound. In the Provisional Specification it is stated that R and R1 may be any group not interfering with the reaction. Specification 642,159 is referred to.
GB28381/47A 1947-10-23 1947-10-23 Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers Expired GB643089A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB28381/47A GB643089A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers
FR989971D FR989971A (en) 1947-10-23 1949-06-30 Process for the preparation of 2: 6-dihalodiphenyl ethers and resulting products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB28381/47A GB643089A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers

Publications (1)

Publication Number Publication Date
GB643089A true GB643089A (en) 1950-09-15

Family

ID=10274753

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28381/47A Expired GB643089A (en) 1947-10-23 1947-10-23 Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers

Country Status (2)

Country Link
FR (1) FR989971A (en)
GB (1) GB643089A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736576A (en) * 1996-06-04 1998-04-07 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US5922775A (en) * 1997-10-23 1999-07-13 Octamer, Inc. Method of treating malignant tumors with ketone thyroxine analogues having no significant hormonal activity
US6017958A (en) * 1996-06-04 2000-01-25 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US7189856B2 (en) 2001-12-28 2007-03-13 Gideon Shapiro Non-peptide somatostatin receptor ligands
US7199265B2 (en) * 2000-06-21 2007-04-03 Karo Bio Ab Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5736576A (en) * 1996-06-04 1998-04-07 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US6017958A (en) * 1996-06-04 2000-01-25 Octamer, Inc. Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US5922775A (en) * 1997-10-23 1999-07-13 Octamer, Inc. Method of treating malignant tumors with ketone thyroxine analogues having no significant hormonal activity
US7199265B2 (en) * 2000-06-21 2007-04-03 Karo Bio Ab Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones
US7189856B2 (en) 2001-12-28 2007-03-13 Gideon Shapiro Non-peptide somatostatin receptor ligands

Also Published As

Publication number Publication date
FR989971A (en) 1951-09-25

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