DE2530003C3 - Verfahren zur Herstellung von tertiären Propargylaminen - Google Patents
Verfahren zur Herstellung von tertiären PropargylaminenInfo
- Publication number
- DE2530003C3 DE2530003C3 DE19752530003 DE2530003A DE2530003C3 DE 2530003 C3 DE2530003 C3 DE 2530003C3 DE 19752530003 DE19752530003 DE 19752530003 DE 2530003 A DE2530003 A DE 2530003A DE 2530003 C3 DE2530003 C3 DE 2530003C3
- Authority
- DE
- Germany
- Prior art keywords
- tertiary
- propargylamines
- preparation
- ammonia
- product
- 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 claims description 6
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical group NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical group OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 2
- QSILYWCNPOLKPN-UHFFFAOYSA-N 3-chloro-3-methylbut-1-yne Chemical compound CC(C)(Cl)C#C QSILYWCNPOLKPN-UHFFFAOYSA-N 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 150000005375 primary alkyl halides Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2478974A IT1015666B (it) | 1974-07-04 | 1974-07-04 | Processo per la preparazione di ammine propargiliche e prodotti cosi ottenuti |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2530003A1 DE2530003A1 (de) | 1976-01-22 |
| DE2530003B2 DE2530003B2 (de) | 1978-04-06 |
| DE2530003C3 true DE2530003C3 (de) | 1985-03-14 |
Family
ID=11214745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752530003 Expired DE2530003C3 (de) | 1974-07-04 | 1975-07-04 | Verfahren zur Herstellung von tertiären Propargylaminen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5129405A (ref) |
| AT (1) | AT339269B (ref) |
| BE (1) | BE830915A (ref) |
| DE (1) | DE2530003C3 (ref) |
| ES (1) | ES439392A1 (ref) |
| FR (1) | FR2277073A1 (ref) |
| GB (1) | GB1485916A (ref) |
| IT (1) | IT1015666B (ref) |
| NL (1) | NL174458C (ref) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107540566A (zh) * | 2017-08-28 | 2018-01-05 | 江苏绿叶农化有限公司 | 一种炔苯酰草胺的制备方法 |
-
1974
- 1974-07-04 IT IT2478974A patent/IT1015666B/it active
-
1975
- 1975-06-19 GB GB2620275A patent/GB1485916A/en not_active Expired
- 1975-06-30 FR FR7520483A patent/FR2277073A1/fr not_active Withdrawn
- 1975-07-02 BE BE157905A patent/BE830915A/xx not_active IP Right Cessation
- 1975-07-03 NL NL7507959A patent/NL174458C/xx not_active IP Right Cessation
- 1975-07-03 ES ES439392A patent/ES439392A1/es not_active Expired
- 1975-07-03 AT AT513875A patent/AT339269B/de not_active IP Right Cessation
- 1975-07-04 DE DE19752530003 patent/DE2530003C3/de not_active Expired
- 1975-07-04 JP JP8198875A patent/JPS5129405A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7507959A (nl) | 1976-01-06 |
| DE2530003B2 (de) | 1978-04-06 |
| FR2277073B1 (ref) | |
| BE830915A (fr) | 1975-11-03 |
| DE2530003A1 (de) | 1976-01-22 |
| IT1015666B (it) | 1977-05-20 |
| ATA513875A (de) | 1977-02-15 |
| NL174458C (nl) | 1984-06-18 |
| GB1485916A (en) | 1977-09-14 |
| JPS5129405A (en) | 1976-03-12 |
| JPS5744656B2 (ref) | 1982-09-22 |
| AT339269B (de) | 1977-10-10 |
| ES439392A1 (es) | 1977-04-16 |
| FR2277073A1 (fr) | 1976-01-30 |
| NL174458B (nl) | 1984-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8228 | New agent |
Free format text: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. KLINGSEISEN, F., DIPL.-ING. ZUMSTEIN JUN., F., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8281 | Inventor (new situation) |
Free format text: STRAZIOTA, MAURIZIO, DR., MAILAND / MILANO, IT |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |