GB2322857A - Nitration of aromatic compounds - Google Patents
Nitration of aromatic compoundsInfo
- Publication number
- GB2322857A GB2322857A GB9811567A GB9811567A GB2322857A GB 2322857 A GB2322857 A GB 2322857A GB 9811567 A GB9811567 A GB 9811567A GB 9811567 A GB9811567 A GB 9811567A GB 2322857 A GB2322857 A GB 2322857A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphilimine
- alkali metal
- reacting
- electron
- acid
- 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.)
- Granted
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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/16—Halogen atoms; Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method of nitrating electron-deficient carbocyclic or heterocyclic aromatic compounds such as pyridines, diazines and triazines and benzenoid aromatics having electron-withdrawing substituents involves first reacting the aromatic species with a sulphilimine species or with the corresponding N-alkali metal salt thereof to generate an N-(hetero)aryl-S,S-dialkyl, diaryl or alkylarysulphilimine derivative. This intermediate may then be readily oxidised under relatively mild conditions using a peroxycarboxylic acid such as m-chloroperbenzoic acid, peracetic or peroxytrifluoroacetic acid. Good yields of nitrated products are obtained including some previously unprepared. The novel N-alkali(alkylaryl)sulphilimine reagents are prepared by reacting an alkali metal hydride, an alkali metal hydrogenous base or an alkyl lithium with the corresponding sulphilimine. Preferred salts are the N-lithio types and the preferred sulphilimine is diphenylsulphilimine. Where the salt is used reaction should be in an aprotic solvent but if the sulphilimine per se is the reagent a polar solvent is used.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9525789A GB2308119A (en) | 1995-12-16 | 1995-12-16 | Nitration of aromatic compounds sulphilimines |
PCT/GB1996/003020 WO1997022590A1 (en) | 1995-12-16 | 1996-12-09 | Nitration of aromatic compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
GB9811567D0 GB9811567D0 (en) | 1998-07-29 |
GB2322857A true GB2322857A (en) | 1998-09-09 |
GB2322857B GB2322857B (en) | 2000-03-29 |
Family
ID=10785573
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9525789A Withdrawn GB2308119A (en) | 1995-12-16 | 1995-12-16 | Nitration of aromatic compounds sulphilimines |
GB9811567A Expired - Fee Related GB2322857B (en) | 1995-12-16 | 1996-12-09 | Nitration of aromatic compounds |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9525789A Withdrawn GB2308119A (en) | 1995-12-16 | 1995-12-16 | Nitration of aromatic compounds sulphilimines |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1021412A1 (en) |
CA (1) | CA2240644A1 (en) |
CZ (1) | CZ291529B6 (en) |
GB (2) | GB2308119A (en) |
IL (1) | IL124960A (en) |
NO (1) | NO309524B1 (en) |
WO (1) | WO1997022590A1 (en) |
ZA (1) | ZA9610559B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2491225B (en) * | 2010-03-16 | 2013-05-01 | Qinetiq Ltd | MEMS detonator |
CN110330432B (en) * | 2019-07-29 | 2022-07-29 | 重庆医药高等专科学校 | Synthetic method of aromatic nitro compound |
-
1995
- 1995-12-16 GB GB9525789A patent/GB2308119A/en not_active Withdrawn
-
1996
- 1996-12-09 GB GB9811567A patent/GB2322857B/en not_active Expired - Fee Related
- 1996-12-09 CZ CZ19981867A patent/CZ291529B6/en not_active IP Right Cessation
- 1996-12-09 WO PCT/GB1996/003020 patent/WO1997022590A1/en not_active Application Discontinuation
- 1996-12-09 CA CA002240644A patent/CA2240644A1/en not_active Abandoned
- 1996-12-09 EP EP96941744A patent/EP1021412A1/en not_active Withdrawn
- 1996-12-09 IL IL12496096A patent/IL124960A/en not_active IP Right Cessation
- 1996-12-13 ZA ZA9610559A patent/ZA9610559B/en unknown
-
1998
- 1998-06-15 NO NO982753A patent/NO309524B1/en unknown
Non-Patent Citations (4)
Title |
---|
CHEMICAL REVIEWS, vol.77, 1977, pages 409-435 * |
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.23, 1986, pages 421-423 * |
JOURNAL OF ORGANIC CHEMISTRY, vol.47, 1982, pages 552-555 * |
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol.26, no.3, 1994, pages 331-336 * |
Also Published As
Publication number | Publication date |
---|---|
GB2322857B (en) | 2000-03-29 |
IL124960A (en) | 2003-02-12 |
GB2308119A (en) | 1997-06-18 |
NO982753L (en) | 1998-08-17 |
NO309524B1 (en) | 2001-02-12 |
GB9525789D0 (en) | 1996-02-14 |
NO982753D0 (en) | 1998-06-15 |
ZA9610559B (en) | 1997-06-24 |
CA2240644A1 (en) | 1997-06-26 |
GB9811567D0 (en) | 1998-07-29 |
EP1021412A1 (en) | 2000-07-26 |
CZ291529B6 (en) | 2003-03-12 |
WO1997022590A1 (en) | 1997-06-26 |
IL124960A0 (en) | 1999-01-26 |
CZ186798A3 (en) | 1998-10-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20071209 |