CA1297498C - Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine - Google Patents

Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine

Info

Publication number: CA1297498C
Authority: CA; Canada
Prior art keywords: diaminopropane; tetrahydropyrimidine; aminopropylpivalamide; butyl; reaction
Prior art date: 1983-03-04
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 - Fee Related

Application number

CA000422862A

Other languages

English (en)

Inventor

Richard G. Pews

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date 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 date listed.)

1983-03-04

Filing date

1983-03-04

Publication date

1992-03-17

1983-03-04 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1983-03-04 Priority to CA000422862A priority Critical patent/CA1297498C/fr

1988-10-11 Priority to CA000579779A priority patent/CA1303040C/fr

1992-03-17 Application granted granted Critical

1992-03-17 Publication of CA1297498C publication Critical patent/CA1297498C/fr

2009-03-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

GXZZIRGOAFXVBC-UHFFFAOYSA-N 6-amino-2,2-dimethylhexanamide Chemical class NC(=O)C(C)(C)CCCCN GXZZIRGOAFXVBC-UHFFFAOYSA-N 0.000 title claims abstract description 12
238000000034 method Methods 0.000 title claims description 6
PSOCGIYZGWCHCD-UHFFFAOYSA-N 2-tert-butyl-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)(C)C1=NCCCN1 PSOCGIYZGWCHCD-UHFFFAOYSA-N 0.000 title description 4
238000002360 preparation method Methods 0.000 title description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims abstract description 34
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims abstract description 6
238000009835 boiling Methods 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 7
238000004821 distillation Methods 0.000 claims description 5
CYEGSNCGVMQQOP-UHFFFAOYSA-N 2-tert-butyl-1,2,3,4-tetrahydropyrimidine Chemical compound CC(C)(C)C1NCC=CN1 CYEGSNCGVMQQOP-UHFFFAOYSA-N 0.000 abstract description 4
239000002904 solvent Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
RWILRFIHGJCSIP-UHFFFAOYSA-N n-[3-(2,2-dimethylpropanoylamino)propyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCCCNC(=O)C(C)(C)C RWILRFIHGJCSIP-UHFFFAOYSA-N 0.000 description 3
238000010408 sweeping Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
PXEJBTJCBLQUKS-UHFFFAOYSA-N 2-tert-butylpyrimidine Chemical compound CC(C)(C)C1=NC=CC=N1 PXEJBTJCBLQUKS-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
-1 ester amides Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
229940078552 o-xylene Drugs 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000005326 tetrahydropyrimidines Chemical class 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
NTJDIRPMZZMYMU-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CN[C]=NC1 NTJDIRPMZZMYMU-UHFFFAOYSA-N 0.000 description 1
VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 description 1
KZCLFWYVLDNEMU-UHFFFAOYSA-N 2-propan-2-yl-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)C1=NCCCN1 KZCLFWYVLDNEMU-UHFFFAOYSA-N 0.000 description 1
BGNWXRJWDQHCRB-UHFFFAOYSA-N 2-propan-2-ylpyrimidine Chemical compound CC(C)C1=NC=CC=N1 BGNWXRJWDQHCRB-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000422862A 1982-09-27 1983-03-04 Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine Expired - Fee Related CA1297498C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA000422862A CA1297498C (fr)	1983-03-04	1983-03-04	Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine
CA000579779A CA1303040C (fr)	1982-09-27	1988-10-11	N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000422862A CA1297498C (fr)	1983-03-04	1983-03-04	Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000579779A Division CA1303040C (fr)	1982-09-27	1988-10-11	N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines

Publications (1)

Publication Number	Publication Date
CA1297498C true CA1297498C (fr)	1992-03-17

Family

ID=4124709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000422862A Expired - Fee Related CA1297498C (fr)	1982-09-27	1983-03-04	Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine

Country Status (1)

Country	Link
CA (1)	CA1297498C (fr)

1983
- 1983-03-04 CA CA000422862A patent/CA1297498C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1994-09-17	MKLA	Lapsed

Publication	Publication Date	Title
EP0649850A1 (fr)	1995-04-26	Procédé de préparation d'isocyanatoorganosilanes
EP0117882A1 (fr)	1984-09-12	Aminopropylpivalamides et leur méthode de préparation
EP0193973B1 (fr)	1988-07-06	Méthode de préparation de 2-alcoylpyrimidine par déshydrogenation de 2-alcoyltetrahydropyrimidine
CA1297498C (fr)	1992-03-17	Aminopropylpivalamides, methode pour leur preparation et leur utilisation pour la fabrication de la 2-t-butyl-1,4,5,6,-tetrahydropyrimidine
CA1303040C (fr)	1992-06-09	N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines
EP0458216B1 (fr)	1994-08-10	Procédé de fabrication de la méthylisobutylcétone
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EP0547092B1 (fr)	1996-12-18	Procede de preparation de 2-methyle-3,5-dialkylpyridines par desalkylation au soufre
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US5214162A (en)	1993-05-25	Process for manufacturing 5-cyano-4-lower alkyloxazoles
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JPH0532388B2 (fr)	1993-05-14
US4730043A (en)	1988-03-08	Process for preparing pyrimidine
JPH04234853A (ja)	1992-08-24	２−アルキルピリミジンの製造方法
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US4605797A (en)	1986-08-12	Hydrogenation catalysts and selective hydrogenation therewith
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EP0123362B1 (fr)	1987-08-05	Procédé de préparation de 6-methylpyridin-2-one
US3711532A (en)	1973-01-16	Preparation of beta-halogenopropionitriles