US4257976A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Resolution process using L or D N-methyl-ephedrine
Assignee: ROSSEL UCLAF
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Filing: 1979-11-20
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Granted: 1981-03-24
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Expires: 1999-11-20
Abstract
Abstract A process for the resolution of DL-cis chrysanthemic acid or DL-trans chrysanthemic acid with L or D N-methyl-ephedrine to form the corresponding salt and acid hydrolyzing the same which resolved acids are intermediates for preparing esters having a remarkable insecticidal activity.
Inventors
- 👤 Charles Pavan
- 👤 Jacques Bulidon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 03:12
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/42; C07C51/487
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
57 words
A process for the resolution of DL-cis or DL-trans chrysanthemic acids comprises reacting DL-cis or DL-trans chrysanthemic acid with D or L N-methyl-ephedrine in an organic solvent, recovering the crystallized salt of LN-methyl-ephedrine and D-cis or D-trans chrysanthemic acid or DN-methyl-ephedrine and L-cis or L-trans chrysanthemic acid and recovering from the salt the corresponding resolved chrysanthemic acid.
Claim 2
Dependent Claim
57 words
A process for the resolution of DL-cis or DL-trans chrysanthemic acids comprises reacting DL-cis or DL-trans chrysanthemic acid with D or L N-methyl-ephedrine in an organic solvent, recovering the crystallized salt of LN-methyl-ephedrine and D-cis or D-trans chrysanthemic acid or DN-methyl-ephedrine and L-cis or L-trans chrysanthemic acid and recovering from the salt the corresponding resolved chrysanthemic acid.
Claim 3
Dependent Claim
42 words
The process of claim 1 wherein DL-cis chrysanthemic acid is reacted with L or D N-methyl-ephedrine, the salt of L N-methyl-ephedrine D-cis chrysanthemic acid or D N-methyl-ephedrine and L-cis chrysanthemic acid crystallizes and D-cis chrysanthemic acid or L-cis chrysanthemic acid is recovered.
Claim 4
Dependent Claim
23 words
The process of claim 2 wherein the solvent is selected from the group consisting of toluene, ethyl acetate, acetone, isopropanol and isopropyl ether.
Claim 5
Dependent Claim
11 words
The process of claim 2 wherein the solvent is isopropyl ether.
Claim 6
Dependent Claim
10 words
The process of claim 2 wherein the solvent is toluene.
Claim 7
Dependent Claim
43 words
The process of claim 1 wherein DL-trans chrysanthemic acid is reacted with L or D N-methyl-ephedrine, the salt of L N-methyl-ephedrine and D-trans chrysanthemic acid or D N-methyl-ephedrine and L-trans chrysanthemic acid crystallizes and D-trans chrysanthemic acid or L-trans chrysanthemic acid is recovered.
Claim 8
Dependent Claim
14 words
The process of claim 6 wherein the organic solvent is toluene or isopropyl ether.
Claim 9
Dependent Claim
36 words
The process of claim 1 wherein the mother liquors of crystallization are evaporated to dryness to obtain the non-crystallizing salt of N-methyl-ephedrine and chrysanthemic acid and recovering from the said salt the corresponding resolved chrysanthemic acid.
Claim 10
Dependent Claim
25 words
A compound selected from the group consisting of D N-methyl-ephedrine L-trans chrysanthemate, L N-methyl-ephedrine D-trans chrysanthemate, L N-methyl-ephedrine D-cis chrysanthemate and D N-methyl-ephedrine L-cis chrysanthemate.
Claim 11
Dependent Claim
25 words
A compound selected from the group consisting of D N-methyl-ephedrine L-trans chrysanthemate, L N-methyl-ephedrine D-trans chrysanthemate, L N-methyl-ephedrine D-cis chrysanthemate and D N-methyl-ephedrine L-cis chrysanthemate.
References Cited (Backward Citations)
GB1178423A
Cited
US3646118A
Cited
US3739019A
Cited
US3666798A
Cited
US3879451A
Cited
US3842125A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-23 | 1984-09-22 | 1985-03-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-23 | 1988-09-22 | 1989-03-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-23 | 1992-09-22 | 1993-03-24 | $7700.00 | Window Closed / Lapsed |