← Back to Patent Explorer
US3981869A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of heterocyclic compounds

Assignee: Bayer AG
•
Filing: 1974-08-05
•
Granted: 1976-09-21
•
Expires: 1994-08-05
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Process for the preparation of heterocyclic compounds of the general formula ##SPC1## By condensation of an o-substituted amine of the general formula ##SPC2## With a carbonyl compound of the general formula ##EQU1## in the presence of a hydrazine of the general formula ##EQU2## followed by quaternization if appropriate. In the formulae the radicals have the meaning as indicated below.

Inventors

  • 👤 Peter Ziemek

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 19:24
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/56; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D235/14; C07D277/00; C07D277/60; C07D277/62; C07D277/64; C09; C09B; C09B26/00; C09B26/02; C09B26/04

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 304 words
Process for preparing compounds of the formula ##SPC9## by condensing an amine of the formula ##SPC10## with a carbonyl compound of the formula ##EQU7## in the presence of a hydrazine of the formula ##EQU8## wherein A is a benzene; naphthalene; pyridine; pyrimidine; or a pyrazine ring; or a benzene or naphthalene ring which is substituted with halogen, C 1 -C 4 -alkyl, cyclohexyl, phenyl, C 1 -C 4 -alkoxy, nitro, cyano, amino, C 1 -C 4 -alkyl-carbonylamino, C 1 -C 4 -alkyl-sulphonylamino, C 1 -C 4 -alkyl-sulphonyl, phenylsulphonyl, tolyl-sulphonyl, benzylsulphonyl, hydroxyl, carboxyl, carboalkoxy with 1 to 4 C atoms in the alkoxy group, carbonamide or sulphonamide; X is O, S or N-R 4 ; R 4 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl or naphthyl; R 1 is hydrogen or C 1 -C 4 -alkyl; R 2 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl; naphthyl; or pheyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, halogen, C 1 -C 4 -dialkylamino, or benzyl; R 3 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl; naphthyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, halogen, C 1 -C 4 -dialkylamino, or benzyl; benzthiazolyl-2; benzoxazolyl-2; benzimidazolyl-2; oxazolyl-2; triazolyl-2; thiazolyl-2; thiophenyl-2; purine-2; pyridine-2; pyrimidine-2; cinnolinyl-3; quinoxazinyl-2; or quinazolinyl-2; or R 2 and R 3 conjointly with the N atom form an indoline; carbazole or tetrahydroquinoline radical or one of the foregoing radicals substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen; R is hydrogen, C 1 -C 4 -alkyl; allyl; cyclohexyl; benzyl; phenethyl; phenyl or naphthyl; An - is an anion; X 1 is hydroxyl, methoxy, ethoxy or halogen; and X 2 and X 3 are halogen or conjointly are oxygen.
Claim 2
Dependent Claim 304 words
Process for preparing compounds of the formula ##SPC9## by condensing an amine of the formula ##SPC10## with a carbonyl compound of the formula ##EQU7## in the presence of a hydrazine of the formula ##EQU8## wherein A is a benzene; naphthalene; pyridine; pyrimidine; or a pyrazine ring; or a benzene or naphthalene ring which is substituted with halogen, C 1 -C 4 -alkyl, cyclohexyl, phenyl, C 1 -C 4 -alkoxy, nitro, cyano, amino, C 1 -C 4 -alkyl-carbonylamino, C 1 -C 4 -alkyl-sulphonylamino, C 1 -C 4 -alkyl-sulphonyl, phenylsulphonyl, tolyl-sulphonyl, benzylsulphonyl, hydroxyl, carboxyl, carboalkoxy with 1 to 4 C atoms in the alkoxy group, carbonamide or sulphonamide; X is O, S or N-R 4 ; R 4 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl or naphthyl; R 1 is hydrogen or C 1 -C 4 -alkyl; R 2 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl; naphthyl; or pheyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, halogen, C 1 -C 4 -dialkylamino, or benzyl; R 3 is hydrogen, C 1 -C 4 -alkyl; cyclohexyl; benzyl; phenethyl; phenyl; naphthyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, halogen, C 1 -C 4 -dialkylamino, or benzyl; benzthiazolyl-2; benzoxazolyl-2; benzimidazolyl-2; oxazolyl-2; triazolyl-2; thiazolyl-2; thiophenyl-2; purine-2; pyridine-2; pyrimidine-2; cinnolinyl-3; quinoxazinyl-2; or quinazolinyl-2; or R 2 and R 3 conjointly with the N atom form an indoline; carbazole or tetrahydroquinoline radical or one of the foregoing radicals substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen; R is hydrogen, C 1 -C 4 -alkyl; allyl; cyclohexyl; benzyl; phenethyl; phenyl or naphthyl; An - is an anion; X 1 is hydroxyl, methoxy, ethoxy or halogen; and X 2 and X 3 are halogen or conjointly are oxygen.
Claim 3
Dependent Claim 30 words
Process according to claim 1, characterised in that dyestuffs according to the formula I of claim 1 are prepared in which A denotes a benzene ring and X denotes sulphur.
Claim 4
Dependent Claim 19 words
Process according to claim 1, characterised in that glyoxylic acid or glyoxylic acid derivatives are employed as carbonyl compounds.
Claim 5
Dependent Claim 13 words
Process according to claim 1, characterised in that open-chain 1,1-substituted hydrazines are employed.
Claim 6
Dependent Claim 14 words
Process according to claim 1, characterised in that N-aminoheterocyclic compounds are employed as hydrazines.
Claim 7
Dependent Claim 17 words
Process according to claim 1, characterised in that the reaction is carried out as a one-pot reaction.

References Cited (Backward Citations)

US2522854A Cited
US2504617A Cited
US2710823A Cited
US2872449A Cited
US3795680A Cited
US3406178A Cited
US3401048A Cited
US3417082A Cited
US3586694A Cited
US3769279A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-09-21 1980-03-22 1980-09-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-09-21 1984-03-22 1984-09-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-09-21 1988-03-22 1988-09-21 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag