CA1303040C - N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines - Google Patents

N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines

Info

Publication number: CA1303040C
Authority: CA; Canada
Prior art keywords: propandiylbis; alkylpyrimidines; reaction; diaminopropane; preparing
Prior art date: 1982-09-27
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

CA000579779A

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.)

1982-09-27

Filing date

1988-10-11

Publication date

1992-06-09

1983-01-18 Priority claimed from US06/458,812 external-priority patent/US4493929A/en

1983-03-04 Priority claimed from CA000422862A external-priority patent/CA1297498C/fr

1988-10-11 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1992-06-09 Application granted granted Critical

1992-06-09 Publication of CA1303040C publication Critical patent/CA1303040C/fr

2009-06-09 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 3
XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 title 1
239000003054 catalyst Substances 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
229910000510 noble metal Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000012808 vapor phase Substances 0.000 claims abstract description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
150000003230 pyrimidines Chemical class 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 4
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 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
238000005580 one pot reaction Methods 0.000 abstract description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 9
GXZZIRGOAFXVBC-UHFFFAOYSA-N 6-amino-2,2-dimethylhexanamide Chemical compound NC(=O)C(C)(C)CCCCN GXZZIRGOAFXVBC-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
CYEGSNCGVMQQOP-UHFFFAOYSA-N 2-tert-butyl-1,2,3,4-tetrahydropyrimidine Chemical compound CC(C)(C)C1NCC=CN1 CYEGSNCGVMQQOP-UHFFFAOYSA-N 0.000 description 3
PSOCGIYZGWCHCD-UHFFFAOYSA-N 2-tert-butyl-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)(C)C1=NCCCN1 PSOCGIYZGWCHCD-UHFFFAOYSA-N 0.000 description 3
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
238000001816 cooling Methods 0.000 description 3
229940078552 o-xylene Drugs 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
KZCLFWYVLDNEMU-UHFFFAOYSA-N 2-propan-2-yl-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)C1=NCCCN1 KZCLFWYVLDNEMU-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
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
-1 ester amides Chemical class 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 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
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
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
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-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
BGNWXRJWDQHCRB-UHFFFAOYSA-N 2-propan-2-ylpyrimidine Chemical compound CC(C)C1=NC=CC=N1 BGNWXRJWDQHCRB-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
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
230000000694 effects Effects 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
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
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

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000579779A 1982-09-27 1988-10-11 N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines Expired - Fee Related CA1303040C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US42387782A	1982-09-27	1982-09-27
US06/458,812 US4493929A (en)	1981-09-14	1983-01-18	Preparation of 2-alkylpyrimidines
US458,812		1983-01-18
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
US423,877		1989-10-19

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000422862A Division 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

Publications (1)

Publication Number	Publication Date
CA1303040C true CA1303040C (fr)	1992-06-09

Family

ID=27167332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000579779A Expired - Fee Related 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

Country Status (1)

Country	Link
CA (1)	CA1303040C (fr)

1988
- 1988-10-11 CA CA000579779A patent/CA1303040C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1994-12-09	MKLA	Lapsed

Publication	Publication Date	Title
EP0117882A1 (fr)	1984-09-12	Aminopropylpivalamides et leur méthode de préparation
JPH0567635B2 (fr)	1993-09-27
EP0193973B1 (fr)	1988-07-06	Méthode de préparation de 2-alcoylpyrimidine par déshydrogenation de 2-alcoyltetrahydropyrimidine
CA1303040C (fr)	1992-06-09	N,n'-1,3-propanediyl-bis-(2,2-dimethylpropanamide) et procede pour la preparation de 2-alkylpyrimidines
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
US5235051A (en)	1993-08-10	Pyridinium salts containing alkoxysilyl groups
EP1065198B1 (fr)	2003-09-17	Procédé pour la préparation de malononitrile
EP0458216A1 (fr)	1991-11-27	Procédé de fabrication de la méthylisobutylcétone
US5214162A (en)	1993-05-25	Process for manufacturing 5-cyano-4-lower alkyloxazoles
EP0547092B1 (fr)	1996-12-18	Procede de preparation de 2-methyle-3,5-dialkylpyridines par desalkylation au soufre
EP0159637B1 (fr)	1990-03-07	Procédé de préparation d'anhydrides phtaliques substitués en position 4
US3804840A (en)	1974-04-16	Manufacture of halogenated pyridine derivatives
JPH04234836A (ja)	1992-08-24	Ｎ，ｎ′−１，３−プロパンジイルビス（２，２−ジメチルプロパンアミド）
US4549995A (en)	1985-10-29	Process for making alkanephosphonous acid esters
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
US5210344A (en)	1993-05-11	Dehydrohalogenation of 1,1,2-trichloroethane using cyclic amines
JPS63243064A (ja)	1988-10-07	ベンゾニトリル類の製法
US4845301A (en)	1989-07-04	Process for the preparation of α-hdroxyketones
US5189166A (en)	1993-02-23	Process for the preparation of 2-alkyl-5-hydroxypyrimidines from 1,3-diamino-2-propanol and an alkanecarboxylic acid
JP3001626B2 (ja)	2000-01-24	２―クロロプロピオンアルデヒド三量体およびその製造方法
EP0123362B1 (fr)	1987-08-05	Procédé de préparation de 6-methylpyridin-2-one
US3354165A (en)	1967-11-21	Akylation of pyridine compounds
Hull Jr et al.	1992	Multigram preparation of 2-alkylpyrimidines in the vapor phase from carboxylic acids and 1, 3-diaminopropane over a dual catalyst system
US4999427A (en)	1991-03-12	Process for the preparation of 2-alkylpyrimidines