CA1251794A - Synthese de 2-vinyl-4,6-diamino-s-triazine - Google Patents

Synthese de 2-vinyl-4,6-diamino-s-triazine

Info

Publication number: CA1251794A
Authority: CA; Canada
Prior art keywords: triazine; diamino; process according; reduced pressure; imidazolyl
Prior art date: 1985-01-11
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

Application number

CA000471897A

Other languages

English (en)

Inventor

Takeshi Masuda

Natsuo Sawa

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.)

Shikoku Chemicals Corp

Original Assignee

Shikoku Chemicals Corp

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.)

1985-01-11

Filing date

1985-01-11

Publication date

1989-03-28

1985-01-11 Application filed by Shikoku Chemicals Corp filed Critical Shikoku Chemicals Corp

1985-01-11 Priority to CA000471897A priority Critical patent/CA1251794A/fr

1989-03-28 Application granted granted Critical

1989-03-28 Publication of CA1251794A publication Critical patent/CA1251794A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 34
ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 title claims abstract description 9
230000015572 biosynthetic process Effects 0.000 title claims abstract description 6
238000003786 synthesis reaction Methods 0.000 title claims abstract description 6
-1 imidazolyl-S-triazine compound Chemical class 0.000 claims abstract description 19
238000010438 heat treatment Methods 0.000 claims abstract description 15
238000006116 polymerization reaction Methods 0.000 claims abstract description 10
239000003112 inhibitor Substances 0.000 claims abstract description 9
VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical compound [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
239000000843 powder Substances 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
239000006004 Quartz sand Substances 0.000 claims description 3
229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
239000000126 substance Substances 0.000 description 9
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000000859 sublimation Methods 0.000 description 8
230000008022 sublimation Effects 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000013078 crystal Substances 0.000 description 6
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000007792 addition Methods 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000004576 sand Substances 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000010951 brass Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)

CA000471897A 1985-01-11 1985-01-11 Synthese de 2-vinyl-4,6-diamino-s-triazine Expired CA1251794A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000471897A CA1251794A (fr)	1985-01-11	1985-01-11	Synthese de 2-vinyl-4,6-diamino-s-triazine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000471897A CA1251794A (fr)	1985-01-11	1985-01-11	Synthese de 2-vinyl-4,6-diamino-s-triazine

Publications (1)

Publication Number	Publication Date
CA1251794A true CA1251794A (fr)	1989-03-28

Family

ID=4129555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000471897A Expired CA1251794A (fr)	1985-01-11	1985-01-11	Synthese de 2-vinyl-4,6-diamino-s-triazine

Country Status (1)

Country	Link
CA (1)	CA1251794A (fr)

1985
- 1985-01-11 CA CA000471897A patent/CA1251794A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-03-28	MKEX	Expiry

Publication	Publication Date	Title
JP2857219B2 (ja)	1999-02-17	２―（２’，４’―ジヒドロキシフエニル）―４，６―ジアリール―ｓ―トリアジンの製造方法
CA1251794A (fr)	1989-03-28	Synthese de 2-vinyl-4,6-diamino-s-triazine
US4579946A (en)	1986-04-01	Process for synthesis of 2-vinyl-4,6-diamino-S-triazine
EP0188039B1 (fr)	1989-08-09	Méthode pour la synthèse de la 2-vinyl-4,6 diamino-S-triazine
EP0420991B1 (fr)	1996-02-28	Procede de production d'un compose bis(1,2-diaryl-1,2-ethylenedithiolato)nickel
CA1171081A (fr)	1984-07-17	Production de derives de la purine et produits intermediaires a cet effet
US3794636A (en)	1974-02-26	Process for preparation of thiazole hydrohalides
JPS6210230B2 (fr)	1987-03-05
JP3817736B2 (ja)	2006-09-06	６−置換−２（１ｈ）−キノキサリノンの製法
CA1251795A (fr)	1989-03-28	Synthese de la 2-vinyl-4,6-diamino-s-triazine
KR900001911B1 (ko)	1990-03-26	2-비닐-4, 6-디아미노-s-트리아진의 합성방법
US2852516A (en)	1958-09-16	Method for preparing amino-formamido compounds
JP3849147B2 (ja)	2006-11-22	ベンゾ〔１，２−ｄ：５，４−ｄ′〕ビス−２（３Ｈ）−オキサゾロン誘導体の製造方法
KR930002215B1 (ko)	1993-03-27	벤즈안트론의 제조 방법
CA2401546C (fr)	2006-09-19	Synthese de derives de la 3-sulfonamido-4-phenylaminopyridine
JPH0365343B2 (fr)	1991-10-11
KR910003708B1 (ko)	1991-06-08	2-비닐-4,6-디아미노-s-트리아진의 합성방법
US3225048A (en)	1965-12-21	Process for the preparation of 2,6-diketo-8-thiapurines
JPS629593B2 (fr)	1987-02-28
JPH0469156B2 (fr)	1992-11-05
JP3893712B2 (ja)	2007-03-14	ジシアノフェノチアジン化合物及びその製造方法
JPS6081144A (ja)	1985-05-09	α−ハロゲノ−β−フエニルプロピオン酸の製造方法
SU1735296A1 (ru)	1992-05-23	Способ получени 1-(2 @ ,4 @ ,6 @ -трихлорфенил)-3-(2 @ -хлор-5 @ -октадецилсукцинимидофениламино)-4-(1 @ -нафтилазо)пиразолона-5 @
EP0211121B1 (fr)	1991-12-11	Procédé pour la synthèse de la 2-vinyl-4,6-diamino-s-triazine
JPS629594B2 (fr)	1987-02-28