Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
  • C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
  • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
  • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
  • C07D263/36—One oxygen atom
  • C07D263/38—One oxygen atom attached in position 2

Definitions

• This invention relates to a process for producing sulfamides, and to novel intermediates used in the process .
• Sulfamides are conventionally prepared by the use of strongly electrophilic reagents such as sulfamoyl chloride, sulfonyl dichloride, phosphorus oxychloride or phosphorus pentachloride .
• Belgian patent 667.311 discloses a method of making sulfamides employing an N-alkyl sulfamoyl chloride.
• all such reagents involve aggressive synthetic methods, and indeed can be inconvenient or dangerous in their practical, industrial, application.
• the invention provides a process for the production of aryl sulfamides that avoids the use of the above hazardous materials and conditions, and gives a high yield.
• the process of the invention is for the production of an aryl sulfamide having the formula O
• ⁇ - , R ⁇ and R 3 are each hydrogen, alkyl
• R 3 is aryl
• R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each hydrogen, alkyl or aryl, and n is 0 or 1, with an amine of the formula
• the reaction can be carried out at ambient temperature or at the reflux temperature of the solvent in which the reaction is performed, and generally the temperature of the reaction is chosen in the range of from 0» C. to
• a polar, aprotic, solvent is preferred, as, for example, acetonitrile .
• a strong base is required for the reaction to proceed, and examples include triethylamine,
• DBN 5-diazabicyclo [4,3,0] non-5-ene
• TED 4-diazabicyclo [2 , 2 , 2] octane
• an alkyl group can be substituted or unsubstituted, and is preferably C ⁇ _g alkyl, being
• a cycloalkyl group preferably containing from 3 to 9 carbon atoms, and may, for example, be substituted by one to three alkyl groups such as methyl.
• the alkyl group can be substituted by halo, C_ _ Q alkoxy, C_ _g cycloalkyl,
• An aryl group can be, for example, naphthyl or, preferably, phenyl, and can be substituted or unsubstituted.
• a substituted aryl group is substituted with one or more, preferably one to three, substituents selected from, for example, an electron-donating substituent such as, for example, C__4 alkyl, C ] __4
• R ⁇ , R ⁇ and R3 are selected from hydrogen, C ⁇ _ alkyl and optionally substituted phenyl.
• R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are preferably hydrogen, and n is preferably 0. It may, nevertheless, be desirable to employ a terminal moiety
• R 4 to R 9 is alkyl or aryl, for instance, in the preparation of stereoisomers .
• substituent R ⁇ is optionally substituted alkyl or phenyl optionally substituted with an electron- donating substituent, and a preferred process is one for the preparation of a compound of the formula O
• R ⁇ - is alkyl or phenyl optionally substituted
• R ⁇ and R ⁇ are each hydrogen, alkyl or optionally substituted phenyl
• R ⁇ is phenyl optionally substituted with
• an electron-donating substituent and/or R ⁇ is optionally substituted phenyl
• a particularly preferred process is one for the production of a compound of the above formula in which R! is C_ _ Q alkyl or phenyl optionally substituted
• R ⁇ is C ⁇ - alkyl
• R ⁇ is phenyl optionally substituted with
• an electron-donating substituent and/or R ⁇ is optionally substituted phenyl.
• Hal is chloro or bromo
• the sulfamides of formula (I) can be put to many uses, One such is disclosed in EP-A 0 897921, in which a sulfamide is cyclised to produce a benzothiadiazine dioxide intermediate employed in the preparation of pharmaceutically active compounds.
• reaction mixture was filtered and the filter cake washed with water (0.2 L) and dried at 50 «C under reduced pressure to yield 90.82 g (0.355 mol) of crude 2-oxo-oxazolidine-3-sulfonic acid (4-methylphenyl) - amide.
• Triethylamine (3.50 ml, 2.55 g, 25.2 mmol, 2.5 equiv) and tert-amylamine (1.50 ml, 1.12 g, 12.8 mmol, 1.3 equiv) were added to a solution of 2-oxo- oxazolidine-3-sulfonic acid (4-methylphenyl) -amide (2.56 g, 10 mmol, 1.0 equiv) in acetonitrile (12.5 ml). This mixture was heated at reflux for 8 h.
• Triethylamine (7.0 ml, 5.10 g, 50 mmol, 2.5 equiv) and 4-methanesulfonyl-phenylamine ( .28 g, 25 mmol, 1.25 equiv) were added to a solution of 2-oxo-oxazolidine-3- sulfonic acid (4-methylphenyl) -amide (5.12 g, 20 mmol) in acetonitrile (25 ml) . This reaction mixture was heated at reflux for 8 hours.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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Publications (1)

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• 1999
  • 1999-11-18 GB GB9927302A patent/GB2356398A/en not_active Withdrawn
• 2000
  • 2000-11-03 AU AU14343/01A patent/AU1434301A/en not_active Abandoned
  • 2000-11-03 CA CA002391978A patent/CA2391978A1/en not_active Abandoned
  • 2000-11-03 JP JP2001538874A patent/JP2003514797A/ja not_active Withdrawn
  • 2000-11-03 WO PCT/US2000/028877 patent/WO2001036383A1/en not_active Application Discontinuation
  • 2000-11-03 EP EP00976591A patent/EP1235795A1/de not_active Withdrawn

Non-Patent Citations (1)

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