ES405171A1 - Process for the preparation of 3- beta-dialkyl-aminoethyl - 4-alkyl -7-carboethoxymethoxycoumarins - Google Patents
Process for the preparation of 3- beta-dialkyl-aminoethyl - 4-alkyl -7-carboethoxymethoxycoumarinsInfo
- Publication number
- ES405171A1 ES405171A1 ES405171A ES405171A ES405171A1 ES 405171 A1 ES405171 A1 ES 405171A1 ES 405171 A ES405171 A ES 405171A ES 405171 A ES405171 A ES 405171A ES 405171 A1 ES405171 A1 ES 405171A1
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- formula
- beta
- alkyl
- indicated above
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 2
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 2
- 239000012433 hydrogen halide Substances 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 1
- 229960001755 resorcinol Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedure for the preparation of chambers and their derivatives, particularly 3- (beta-dialkylaminoethyl) -4-alkyl-7-carbetoxymethoxycoumarins, of general formula: **(See formula)** in which R1, R2 and R3 indicate short-chain alkyls with 1-3 carbon atoms, and their hydrohalides, characterized in that the resorcin is reacted with a gamma-butyrolactone derivative of general formula **(See formula)** wherein R1 has the above meaning, and with hydrogen halide in anhydrous medium of a short-chain aliphatic acid and phosphorous acid (PIII), 3- (beta-halogenoethyl) -4-alkyl-7-hydroxycoumarin obtained of formula general: **(See formula)** Where R1 has the meaning indicated above and X indicates a chlorine or bromine atom, it is reacted with ethyl ester of a halogenoacetic acid of general formula X-CH2CH2COOC2H5 where X indicates a chlorine or bromine atom, in acetone in the presence of an alkali metal carbonate and a catalyst, the 3- (beta-halogenoethyl) -4-alkyl-7-carbetoxymethoxycoumarin produced of the general formula: **(See formula)** Where R1 and X have the meaning indicated above, it is reacted with excess dialkylamine of general formula: **(See formula)** in which R2 and R3 have the meaning indicated above, in the presence of a hydrogen halide acceptor in benzene or toluene, then the reaction mixture is washed with water, the solvent is evaporated, the residue is dissolved in ethanol, the solution it is treated with anhydrous zinc chloride, the mixture with the complex compound precipitate is cooled, the precipitate is separated, the complex compound is decomposed by means of an aqueous solution of alkali metal carbonate or ammonia and the liberated product of general formula (1), in which R1, R2 and R3 have the meaning indicated above, is isolated and, if necessary, converted to hydrohalide. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14953171A PL74614B1 (en) | 1971-07-19 | 1971-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES405171A1 true ES405171A1 (en) | 1975-07-01 |
Family
ID=19955081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES405171A Expired ES405171A1 (en) | 1971-07-19 | 1972-07-12 | Process for the preparation of 3- beta-dialkyl-aminoethyl - 4-alkyl -7-carboethoxymethoxycoumarins |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4875577A (en) |
| DE (1) | DE2235428B2 (en) |
| ES (1) | ES405171A1 (en) |
| GB (1) | GB1362337A (en) |
| PL (1) | PL74614B1 (en) |
| SU (1) | SU511008A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1088554B (en) * | 1977-11-17 | 1985-06-10 | F I D I A Spa | SELLECTIVE PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 7-INDROSSI CUMARINA |
-
1971
- 1971-07-19 PL PL14953171A patent/PL74614B1/xx unknown
-
1972
- 1972-07-03 GB GB3101972A patent/GB1362337A/en not_active Expired
- 1972-07-12 SU SU1809606A patent/SU511008A3/en active
- 1972-07-12 ES ES405171A patent/ES405171A1/en not_active Expired
- 1972-07-18 JP JP7195472A patent/JPS4875577A/ja active Pending
- 1972-07-19 DE DE19722235428 patent/DE2235428B2/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1362337A (en) | 1974-08-07 |
| DE2235428B2 (en) | 1974-01-17 |
| JPS4875577A (en) | 1973-10-11 |
| SU511008A3 (en) | 1976-04-15 |
| PL74614B1 (en) | 1974-12-31 |
| DE2235428A1 (en) | 1973-02-15 |
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