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Process for the preparation of aromatic amines

Assignee: Bayer AG
•
Filing: 1991-04-09
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Granted: 1993-11-16
•
Expires: 2011-04-09
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Abstract

Abstract Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.

Inventors

  • 👤 Mieczyslaw Makosza
  • 👤 Maciej Bialecki

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 02:55
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/73; C07C; C07C209/00; C07C209/02; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/42; C07D333/44

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 214 words
Process for the preparation of aromatic amines of the formula ##STR3## wherein Ar denotes a mono- or polycyclic aromatic radical with 4 to 16 C atoms which can also contain 1 to 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, R denotes hydrogen, C 1 -C 4 -alkyl(optionally substituted by halogen or C 1 -C 4 -alkoxy), C 1 -C 4 -alkenyl, C 5 -C 12 -cycloalkyl, C 5 -C 12 -aryl(optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy), Y denotes nitro in the 2- or 4-position in relation to the amino group --NHR, Z denotes halogen, cyano, optionally halogenated C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, optionally halogenated C 1 -C 4 -alkylmercapto, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulphonyl, carboxyl or hydroxyl and m denotes 1 or 2 and n denotes zero or 1, which comprises reacting compounds of the formula ##STR4## wherein Y denotes nitro and the remaining symbols have the abovementioned meaning, with organic sulphenamides in aprotic organic solvents or in liquid ammonia in the presence of bases at temperatures of -50° to +100° C., the bases being used in a quantity of 2 to 7 mols per mol of starting compound (II).
Claim 2
Dependent Claim 214 words
Process for the preparation of aromatic amines of the formula ##STR3## wherein Ar denotes a mono- or polycyclic aromatic radical with 4 to 16 C atoms which can also contain 1 to 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, R denotes hydrogen, C 1 -C 4 -alkyl(optionally substituted by halogen or C 1 -C 4 -alkoxy), C 1 -C 4 -alkenyl, C 5 -C 12 -cycloalkyl, C 5 -C 12 -aryl(optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy), Y denotes nitro in the 2- or 4-position in relation to the amino group --NHR, Z denotes halogen, cyano, optionally halogenated C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, optionally halogenated C 1 -C 4 -alkylmercapto, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulphonyl, carboxyl or hydroxyl and m denotes 1 or 2 and n denotes zero or 1, which comprises reacting compounds of the formula ##STR4## wherein Y denotes nitro and the remaining symbols have the abovementioned meaning, with organic sulphenamides in aprotic organic solvents or in liquid ammonia in the presence of bases at temperatures of -50° to +100° C., the bases being used in a quantity of 2 to 7 mols per mol of starting compound (II).
Claim 3
Dependent Claim 23 words
Process according to claim 1, wherein the starting compounds (II) and the sulphenamides are reacted in a molar ratio of 0.8 to 1.2.
Claim 4
Dependent Claim 59 words
Process according to claim 1, wherein R denotes C 1 -C 4 -alkyl (optionally substituted by halogen or C 1 -C 4 -alkoxy), C 1 -C 4 -alkenyl, C 5 -C 12 -cycloalkyl, C 5 -C 12 -aryl (optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy), or C 2 -C 6 -acyl.
Claim 5
Dependent Claim 45 words
Process according to claim 1, wherein R denotes C 1 -C 4 -alkyl optionally substituted by halogen or C 1 -C 4 -alkoxy or denotes C 5 -C 12 -aryl optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.

References Cited (Backward Citations)

US2750417A Cited
US4140853A Cited
US4386209A Cited
US4950673A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-11-15 1997-05-17 1997-11-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-11-15 2001-05-17 2001-11-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-11-15 2005-05-17 2005-11-16 $7700.00 Window Closed / Lapsed

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