CS201049B2 - Process for preparing di-n-propylacetamide - Google Patents
Process for preparing di-n-propylacetamide Download PDFInfo
- Publication number
- CS201049B2 CS201049B2 CS773337A CS333777A CS201049B2 CS 201049 B2 CS201049 B2 CS 201049B2 CS 773337 A CS773337 A CS 773337A CS 333777 A CS333777 A CS 333777A CS 201049 B2 CS201049 B2 CS 201049B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- propyl
- temperature
- solution
- acid
- toluene
- Prior art date
Links
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 31
- YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002825 nitriles Chemical class 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 25
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 abstract description 9
- 150000001408 amides Chemical class 0.000 abstract description 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract description 2
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- UZRGQIZTJOPZGE-UHFFFAOYSA-N 2-cyano-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)(C#N)CCC UZRGQIZTJOPZGE-UHFFFAOYSA-N 0.000 description 5
- UMJPVWFIBILILQ-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanamide Chemical compound CC(C)C(C(C)C)C(N)=O UMJPVWFIBILILQ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- -1 cyanoacetic acid ester Chemical class 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FSCFMUWAEFAUJX-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C#N)C(C)C FSCFMUWAEFAUJX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VSJZBUJCPNVRET-UHFFFAOYSA-N 2,2-bis(prop-2-enyl)propanedioic acid Chemical compound C=CCC(C(=O)O)(CC=C)C(O)=O VSJZBUJCPNVRET-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DBYQZULGXMMLDF-UHFFFAOYSA-N O=CC(Cl)(Cl)Cl.[K] Chemical compound O=CC(Cl)(Cl)Cl.[K] DBYQZULGXMMLDF-UHFFFAOYSA-N 0.000 description 1
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical group [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- WSNSMPZJJIYZCV-UHFFFAOYSA-N [Na]C Chemical compound [Na]C WSNSMPZJJIYZCV-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 230000007177 brain activity Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7707586A FR2383918A1 (fr) | 1977-03-15 | 1977-03-15 | Nouveau procede de preparation d'un derive de l'acetamide et derive obtenu par ce procede |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201049B2 true CS201049B2 (en) | 1980-10-31 |
Family
ID=9188071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773337A CS201049B2 (en) | 1977-03-15 | 1977-05-20 | Process for preparing di-n-propylacetamide |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4127607A (en, 2012) |
| JP (1) | JPS53112805A (en, 2012) |
| AR (1) | AR212998A1 (en, 2012) |
| AT (1) | AT351010B (en, 2012) |
| AU (1) | AU506864B2 (en, 2012) |
| BE (1) | BE854487A (en, 2012) |
| CA (1) | CA1064518A (en, 2012) |
| CH (1) | CH602590A5 (en, 2012) |
| CS (1) | CS201049B2 (en, 2012) |
| DD (1) | DD130657A5 (en, 2012) |
| DE (1) | DE2721261C3 (en, 2012) |
| DK (1) | DK147939C (en, 2012) |
| ES (1) | ES467126A1 (en, 2012) |
| FI (1) | FI64577C (en, 2012) |
| FR (1) | FR2383918A1 (en, 2012) |
| GB (1) | GB1522449A (en, 2012) |
| GR (1) | GR60580B (en, 2012) |
| HU (1) | HU175254B (en, 2012) |
| IE (1) | IE45150B1 (en, 2012) |
| IL (1) | IL52022A (en, 2012) |
| IN (1) | IN145512B (en, 2012) |
| IT (1) | IT1080753B (en, 2012) |
| LU (1) | LU77304A1 (en, 2012) |
| MX (1) | MX4568E (en, 2012) |
| NL (1) | NL7705563A (en, 2012) |
| NO (1) | NO144792C (en, 2012) |
| NZ (1) | NZ184327A (en, 2012) |
| OA (1) | OA05694A (en, 2012) |
| PL (1) | PL113489B1 (en, 2012) |
| PT (1) | PT66541B (en, 2012) |
| SE (1) | SE427179B (en, 2012) |
| SU (1) | SU706022A3 (en, 2012) |
| YU (1) | YU40675B (en, 2012) |
| ZA (1) | ZA773777B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5432284A (en) * | 1993-09-08 | 1995-07-11 | G. D. Searle & Co. | Process for the preparation of heterocyclic alkylamide derivatives |
| NZ597253A (en) | 2006-05-24 | 2013-06-28 | Resmed Motor Technologies Inc | Compact low noise efficient blower for CPAP devices |
| CN114763328B (zh) * | 2022-02-14 | 2023-03-17 | 湖南大学 | 一种2-氰基-2-丙戊酸的制备方法与应用 |
-
1977
- 1977-03-15 FR FR7707586A patent/FR2383918A1/fr active Granted
- 1977-04-25 IN IN619/CAL/77A patent/IN145512B/en unknown
- 1977-05-04 NO NO771577A patent/NO144792C/no unknown
- 1977-05-04 DK DK195977A patent/DK147939C/da not_active IP Right Cessation
- 1977-05-05 SE SE7705256A patent/SE427179B/xx not_active IP Right Cessation
- 1977-05-05 IL IL52022A patent/IL52022A/xx unknown
- 1977-05-06 GR GR53387A patent/GR60580B/el unknown
- 1977-05-09 LU LU77304A patent/LU77304A1/xx unknown
- 1977-05-10 HU HU77LA915A patent/HU175254B/hu not_active IP Right Cessation
- 1977-05-10 CA CA278,077A patent/CA1064518A/en not_active Expired
- 1977-05-11 DE DE2721261A patent/DE2721261C3/de not_active Expired
- 1977-05-11 BE BE177458A patent/BE854487A/xx not_active IP Right Cessation
- 1977-05-12 CH CH596377A patent/CH602590A5/xx not_active IP Right Cessation
- 1977-05-13 PT PT66541A patent/PT66541B/pt unknown
- 1977-05-20 AR AR267717A patent/AR212998A1/es active
- 1977-05-20 NL NL7705563A patent/NL7705563A/xx not_active Application Discontinuation
- 1977-05-20 CS CS773337A patent/CS201049B2/cs unknown
- 1977-05-23 JP JP6034177A patent/JPS53112805A/ja active Granted
- 1977-05-25 US US05/800,345 patent/US4127607A/en not_active Expired - Lifetime
- 1977-05-26 DD DD7700199166A patent/DD130657A5/xx not_active IP Right Cessation
- 1977-05-31 PL PL1977198560A patent/PL113489B1/pl unknown
- 1977-06-03 GB GB23782/77A patent/GB1522449A/en not_active Expired
- 1977-06-03 MX MX775780U patent/MX4568E/es unknown
- 1977-06-03 FI FI771782A patent/FI64577C/fi not_active IP Right Cessation
- 1977-06-06 SU SU772488998A patent/SU706022A3/ru active
- 1977-06-08 NZ NZ184327A patent/NZ184327A/xx unknown
- 1977-06-15 YU YU1491/77A patent/YU40675B/xx unknown
- 1977-06-21 IE IE1271/77A patent/IE45150B1/en not_active IP Right Cessation
- 1977-06-21 AU AU26264/77A patent/AU506864B2/en not_active Expired
- 1977-06-23 ZA ZA00773777A patent/ZA773777B/xx unknown
- 1977-06-27 OA OA56206A patent/OA05694A/xx unknown
- 1977-07-04 AT AT475877A patent/AT351010B/de not_active IP Right Cessation
- 1977-07-11 IT IT25583/77A patent/IT1080753B/it active
-
1978
- 1978-02-20 ES ES467126A patent/ES467126A1/es not_active Expired
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