FI71304C - Foerfarande foer framstaellning av ett disubstituerat (n-cyanimido)karbonat - Google Patents

Foerfarande foer framstaellning av ett disubstituerat (n-cyanimido)karbonat Download PDF

Info

Publication number: FI71304C
Authority: FI; Finland
Prior art keywords: water; solution; mixture; toluene; temperature
Prior art date: 1979-01-26

Application number

FI800222A

Other languages

English (en)

Finnish (fi)

Other versions

FI71304B (fi

FI800222A7 (fi

Inventor

Graham Ernest Robinson

Original Assignee

Ici Ltd

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.)

1979-01-26

Filing date

1980-01-25

Publication date

1986-12-19

1980-01-25 Application filed by Ici Ltd filed Critical Ici Ltd

1980-07-27 Publication of FI800222A7 publication Critical patent/FI800222A7/fi

1986-09-09 Publication of FI71304B publication Critical patent/FI71304B/fi

1986-12-19 Application granted granted Critical

1986-12-19 Publication of FI71304C publication Critical patent/FI71304C/fi

Links

BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 86
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
239000000243 solution Substances 0.000 description 46
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
239000007864 aqueous solution Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
ZOKYZTUQSVAKHS-UHFFFAOYSA-N dimethoxymethylidenecyanamide Chemical compound COC(OC)=NC#N ZOKYZTUQSVAKHS-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000126 substance Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XMDCYZRDFRTBQH-UHFFFAOYSA-N 3-bromonaphthalen-2-amine Chemical compound C1=CC=C2C=C(Br)C(N)=CC2=C1 XMDCYZRDFRTBQH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003485 histamine H2 receptor antagonist Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
IOPGBGMYUPEGOK-UHFFFAOYSA-N diethoxymethanimine Chemical compound CCOC(=N)OCC IOPGBGMYUPEGOK-UHFFFAOYSA-N 0.000 description 1
-1 e.g. Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyesters Or Polycarbonates (AREA)
Saccharide Compounds (AREA)

FI800222A 1979-01-26 1980-01-25 Foerfarande foer framstaellning av ett disubstituerat (n-cyanimido)karbonat FI71304C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7902932		1979-01-26
GB7902931		1979-01-26
GB7902931		1979-01-26
GB7902932		1979-01-26

Publications (3)

Publication Number	Publication Date
FI800222A7 FI800222A7 (fi)	1980-07-27
FI71304B FI71304B (fi)	1986-09-09
FI71304C true FI71304C (fi)	1986-12-19

Family

ID=26270359

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI800222A FI71304C (fi)	1979-01-26	1980-01-25	Foerfarande foer framstaellning av ett disubstituerat (n-cyanimido)karbonat

Country Status (12)

Country	Link
US (1)	US4298544A (da)
EP (2)	EP0042628B1 (da)
AU (1)	AU530819B2 (da)
CA (1)	CA1145348A (da)
DK (1)	DK158305C (da)
ES (1)	ES8102091A1 (da)
FI (1)	FI71304C (da)
IE (1)	IE49355B1 (da)
IL (1)	IL59155A (da)
NO (1)	NO151198C (da)
NZ (1)	NZ192607A (da)
PT (1)	PT70735A (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR8107546A (pt) *	1980-11-25	1982-08-17	Du Pont	Composto de 3-amino-2-alquenilimidatos e processo para preparar o composto
US4515626A (en) *	1982-10-06	1985-05-07	Ciba Geigy Corporation	N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity
JP2884412B2 (ja) *	1988-10-21	1999-04-19	日本バイエルアグロケム株式会社	殺虫性シアノ化合物
US5075443A (en) *	1990-08-03	1991-12-24	Ciba-Geigy Corporation	Preparation of 2-amino-4-alkoxy-s-triazines
US5237084A (en) *	1991-06-19	1993-08-17	Ciba-Geigy Corporation	Preparation of dialkyl (N-cyanoimido)carbonates from dialkyl imidocarbonates and cyanogen halides
DE4123608C1 (da) *	1991-07-17	1992-07-02	Skw Trostberg Ag, 8223 Trostberg, De
WO2003057680A1 (en) *	2001-12-28	2003-07-17	Nippon Carbide Kogyo Kabushiki Kaisha	Process for producing 2-cyanoimino-1,3-thiazolidine
CN104860848B (zh) *	2015-05-29	2016-03-09	盐城凯利药业有限公司	一种n-氰亚胺碳酸二酯的合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA467349A (en) *		1950-08-15	C. Redmon Bryan	Preparation of aliphatic iminocarbonates
US2708189A (en) *	1951-11-30	1955-05-10	Us Rubber Co	Di-alkenyl imido carbonates and polymeric materials derived therefrom
US2881071A (en) *	1957-07-12	1959-04-07	Buckman Labor Inc	Processes for the control of slime-forming and other microorganisms and compositions for use therefor
US4235802A (en) *	1979-08-14	1980-11-25	E. I. Du Pont De Nemours And Company	Propenimidates

1980
- 1980-01-10 IE IE44/80A patent/IE49355B1/en not_active IP Right Cessation
- 1980-01-15 EP EP81105237A patent/EP0042628B1/en not_active Expired
- 1980-01-15 NZ NZ192607A patent/NZ192607A/xx unknown
- 1980-01-15 EP EP80300137A patent/EP0014064B1/en not_active Expired
- 1980-01-18 AU AU54726/80A patent/AU530819B2/en not_active Ceased
- 1980-01-18 IL IL59155A patent/IL59155A/xx not_active IP Right Cessation
- 1980-01-24 US US06/118,066 patent/US4298544A/en not_active Expired - Lifetime
- 1980-01-25 NO NO800185A patent/NO151198C/no unknown
- 1980-01-25 CA CA000344419A patent/CA1145348A/en not_active Expired
- 1980-01-25 PT PT70735A patent/PT70735A/pt not_active IP Right Cessation
- 1980-01-25 ES ES488026A patent/ES8102091A1/es not_active Expired
- 1980-01-25 DK DK031480A patent/DK158305C/da not_active IP Right Cessation
- 1980-01-25 FI FI800222A patent/FI71304C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT70735A (en)	1980-02-01
CA1145348A (en)	1983-04-26
NO151198C (no)	1985-02-27
EP0014064A2 (en)	1980-08-06
EP0042628B1 (en)	1983-11-23
AU530819B2 (en)	1983-07-28
IL59155A (en)	1984-01-31
NO800185L (no)	1980-07-28
FI71304B (fi)	1986-09-09
ES488026A0 (es)	1980-12-16
DK158305B (da)	1990-04-30
IE800044L (en)	1980-07-26
ES8102091A1 (es)	1980-12-16
EP0014064B1 (en)	1982-08-04
EP0014064A3 (en)	1980-10-15
US4298544A (en)	1981-11-03
NZ192607A (en)	1982-03-09
EP0042628A2 (en)	1981-12-30
DK158305C (da)	1990-10-01
IE49355B1 (en)	1985-09-18
AU5472680A (en)	1980-07-31
FI800222A7 (fi)	1980-07-27
EP0042628A3 (en)	1982-01-20
DK31480A (da)	1980-07-27
NO151198B (no)	1984-11-19

Legal Events

Date	Code	Title	Description
1994-04-08	PC	Transfer of assignment of patent	Owner name: ZENECA LIMITED
1997-08-13	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: ZENECA LIMITED

Publication	Publication Date	Title
JP2515427B2 (ja)	1996-07-10	プレウロムチリン類
FI71304B (fi)	1986-09-09	Foerfarande foer framstaellning av ett disubstituerat (n-cyanimido) karbonat
US3931216A (en)	1976-01-06	Process for the manufacture of 2-arylamino-2-imidazoline derivatives and their salts
US4435569A (en)	1984-03-06	5-[Substituted amino methyl]pyrrolo[2,3-d]pyrimidine-4-one
NO895195L (no)	1990-06-25	Fremgangsmaate for fremstilling av piperidinderivater samtmellomprodukter.
US4048168A (en)	1977-09-13	Process for preparing 1-polyhaloalkyl-3,4-dihydro-2-(1H)-quinazolinones
SU950188A3 (ru)	1982-08-07	Способ получени производных 4(5)-меркаптометилимидазолов
US3139455A (en)	1964-06-30	Phenoxyacetamidoximes
NO171848B (no)	1993-02-01	Fremstilling av 4-alkoksy-3-pyrrolin-2-on-1-yl-eddiksyrealkylestere
US4275216A (en)	1981-06-23	Process for preparing 4(5)-hydroxymethyl 5(4)-lower alkyl imidazoles
FI70895C (fi)	1986-10-27	Foerfarande foer framstaellning av vinkaminsyraestrar
AU708059C (en)	2001-08-09	An arthropodicidal oxadiazine intermediate
US4017512A (en)	1977-04-12	Process for producing N-alkylhydroxylamines
EP0483674B1 (en)	1994-12-28	A process for producing an aliphatic amide and salts thereof
KR920004137B1 (ko)	1992-05-25	이미다졸 유도체의 제조방법
US4460775A (en)	1984-07-17	2-(3-Mercapto-1-oxopropyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid derivatives
US4892956A (en)	1990-01-09	5-cyano-4,5-dihydro-3,4-dicarboxypyrazole derivatives
US4536574A (en)	1985-08-20	Preparation of 2-alkylthiomethyl-4-hydroxypyrimidines
US4924001A (en)	1990-05-08	Process for preparing 5-cyano-4, 5-dihydro-3,4-dicarboxypyrazole derivatives
KR870001044B1 (ko)	1987-05-26	디히드로-1,4-옥사티인 유도체의 제조방법
US6300503B1 (en)	2001-10-09	Hydantoin intermediates for the synthesis of omapatrilat and methods for producing and using the same
US4720552A (en)	1988-01-19	Process for the preparation of acid addition salts of 4(5)-methyl-5(4)-thiomethyl imidazole
US6284901B1 (en)	2001-09-04	Dinitrile intermediates for the synthesis of omapatrilat and methods for producing same
KR830002349B1 (ko)	1983-10-24	4-(5)-하이드록시메틸 5(4)-저급알킬이미다졸류의 제조방법
US5164515A (en)	1992-11-17	Chemical compounds