SU516353A3 - Способ получени 1-монозамещенных карбамоил-2-бензимидазолилкарбаматов - Google Patents

Способ получени 1-монозамещенных карбамоил-2-бензимидазолилкарбаматов

Info

Publication number: SU516353A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mol; vacuum; product; filtered; dissolved
Prior art date: 1971-01-25

Application number

SU1742302A

Other languages

English (en)

Russian (ru)

Inventor

Харшани Кальман

Шимай Антал

Тот Геза

Такач Кальман

Боднар Янош

Original Assignee

Хиноин Дьедьсер-Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

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.)

1971-01-25

Filing date

1972-01-24

Publication date

1976-05-30

1972-01-24 Application filed by Хиноин Дьедьсер-Еш Ведьесети Термекек Дьяра Рт (Инопредприятие) filed Critical Хиноин Дьедьсер-Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

1976-05-30 Application granted granted Critical

1976-05-30 Publication of SU516353A3 publication Critical patent/SU516353A3/ru

Links

238000000034 method Methods 0.000 title claims description 11
ASUFTTDIVRHZRH-UHFFFAOYSA-N carbamoyl N-(1H-benzimidazol-2-yl)carbamate Chemical class N1=C(NC2=C1C=CC=C2)NC(OC(N)=O)=O ASUFTTDIVRHZRH-UHFFFAOYSA-N 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
239000000047 product Substances 0.000 claims description 11
ZAIRCVNISFRBHW-UHFFFAOYSA-N 1h-benzimidazol-2-yl n-methylcarbamate Chemical compound C1=CC=C2NC(OC(=O)NC)=NC2=C1 ZAIRCVNISFRBHW-UHFFFAOYSA-N 0.000 claims description 8
239000012467 final product Substances 0.000 claims description 8
238000002844 melting Methods 0.000 claims description 8
230000008018 melting Effects 0.000 claims description 8
238000001953 recrystallisation Methods 0.000 claims description 8
238000003756 stirring Methods 0.000 claims description 8
239000003208 petroleum Substances 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
-1 1-cyclohexylcarbamoyl-2-benzimidazolylmethylcarbamate Chemical compound 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
HCIBKIWZFGWIHC-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) N-butylcarbamate Chemical compound ClC1=C(C(=C(C(=C1OC(NCCCC)=O)Cl)Cl)Cl)Cl HCIBKIWZFGWIHC-UHFFFAOYSA-N 0.000 claims description 4
KMUAXEIMZDKMBH-UHFFFAOYSA-N [1-(butylcarbamoyl)benzimidazol-2-yl]methylcarbamic acid Chemical compound CCCCNC(=O)N1C2=CC=CC=C2N=C1CNC(=O)O KMUAXEIMZDKMBH-UHFFFAOYSA-N 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
239000000203 mixture Substances 0.000 claims 2
XCXHGGHNCWMEFS-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) N-benzylcarbamate Chemical compound ClC1=C(C(=C(C(=C1OC(NCC1=CC=CC=C1)=O)Cl)Cl)Cl)Cl XCXHGGHNCWMEFS-UHFFFAOYSA-N 0.000 claims 1
WFTJCZOBXDNNOZ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) N-cyclohexylcarbamate Chemical compound ClC1=C(C(=C(C(=C1OC(NC1CCCCC1)=O)Cl)Cl)Cl)Cl WFTJCZOBXDNNOZ-UHFFFAOYSA-N 0.000 claims 1
LMDXNEFDKCKNRC-UHFFFAOYSA-N (2,4,5-trichlorophenyl) N-butylcarbamate Chemical compound ClC1=C(C=C(C(=C1)Cl)Cl)OC(NCCCC)=O LMDXNEFDKCKNRC-UHFFFAOYSA-N 0.000 claims 1
KEBUEWXZQBMCNB-UHFFFAOYSA-N 1h-benzimidazol-2-yl carbamate Chemical compound C1=CC=C2NC(OC(=O)N)=NC2=C1 KEBUEWXZQBMCNB-UHFFFAOYSA-N 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000012452 mother liquor Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
LTEOJURFSGNUDI-UHFFFAOYSA-N [1-(butylcarbamoyl)benzimidazol-2-yl]methyl carbamate Chemical compound C1=CC=C2N(C(=O)NCCCC)C(COC(N)=O)=NC2=C1 LTEOJURFSGNUDI-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1742302A 1971-01-25 1972-01-24 Способ получени 1-монозамещенных карбамоил-2-бензимидазолилкарбаматов SU516353A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI001078 HU162382B (mo)	1971-01-25	1971-01-25

Publications (1)

Publication Number	Publication Date
SU516353A3 true SU516353A3 (ru)	1976-05-30

Family

ID=10994400

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1742302A SU516353A3 (ru)	1971-01-25	1972-01-24	Способ получени 1-монозамещенных карбамоил-2-бензимидазолилкарбаматов

Country Status (14)

Country	Link
JP (1)	JPS5024313B1 (mo)
AT (1)	AT313302B (mo)
CA (1)	CA956320A (mo)
CS (1)	CS172473B1 (mo)
DE (1)	DE2200648A1 (mo)
DK (1)	DK129046B (mo)
ES (1)	ES399109A1 (mo)
FR (1)	FR2124845A5 (mo)
GB (1)	GB1346953A (mo)
HU (1)	HU162382B (mo)
NO (1)	NO133231C (mo)
PL (1)	PL84205B1 (mo)
SE (1)	SE376419B (mo)
SU (1)	SU516353A3 (mo)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2303999A1 (de) *	1973-01-27	1974-08-08	Hoechst Ag	Substituierte benzimidazole
JPS54175917U (mo) *	1978-05-31	1979-12-12
JPS6210004A (ja) *	1985-07-05	1987-01-19	Sumitomo Chem Co Ltd	フザリウム病害防除剤

1971
- 1971-01-25 HU HUCI001078 patent/HU162382B/hu unknown
1972
- 1972-01-07 DE DE19722200648 patent/DE2200648A1/de not_active Ceased
- 1972-01-17 DK DK21672A patent/DK129046B/da not_active IP Right Cessation
- 1972-01-17 AT AT35272A patent/AT313302B/de not_active IP Right Cessation
- 1972-01-18 CS CS32572A patent/CS172473B1/cs unknown
- 1972-01-21 SE SE71972A patent/SE376419B/xx unknown
- 1972-01-22 ES ES399109A patent/ES399109A1/es not_active Expired
- 1972-01-24 SU SU1742302A patent/SU516353A3/ru active
- 1972-01-24 CA CA132,999A patent/CA956320A/en not_active Expired
- 1972-01-25 PL PL15308172A patent/PL84205B1/pl unknown
- 1972-01-25 NO NO17472A patent/NO133231C/no unknown
- 1972-01-25 FR FR7202410A patent/FR2124845A5/fr not_active Expired
- 1972-01-25 JP JP47009400A patent/JPS5024313B1/ja active Pending
- 1972-01-25 GB GB347772A patent/GB1346953A/en not_active Expired

Also Published As

Publication number	Publication date
DK129046C (mo)	1975-01-20
GB1346953A (en)	1974-02-13
CS172473B1 (mo)	1977-01-28
NO133231C (mo)	1976-03-31
FR2124845A5 (mo)	1972-09-22
DE2200648A1 (de)	1972-08-10
NO133231B (mo)	1975-12-22
SE376419B (mo)	1975-05-26
DK129046B (da)	1974-08-12
HU162382B (mo)	1973-02-28
JPS5024313B1 (mo)	1975-08-14
CA956320A (en)	1974-10-15
PL84205B1 (en)	1976-03-31
AT313302B (de)	1974-02-11
ES399109A1 (es)	1976-01-01

Publication	Publication Date	Title
SU522802A3 (ru)	1976-07-25	Способ получени пенициллинов или их солей
SU698532A3 (ru)	1979-11-15	Способ получени производных пиридо (1,2-а) пиримидина
SU516353A3 (ru)	1976-05-30	Способ получени 1-монозамещенных карбамоил-2-бензимидазолилкарбаматов
SU784766A3 (ru)	1980-11-30	Способ получени бенз-ацил-бензимидазол(2)-производных
SU458131A3 (ru)	1975-01-25	Способ получени шифровых оснований 7-амино-3-дезацфетоксицефалоспорановой кислоты
SU558644A3 (ru)	1977-05-15	Способ получени имидазолов или их солей
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IL39061A (en)	1974-12-31	Method of preparing nitrobenzyl mesylates and tosylates
US3725422A (en)	1973-04-03	New organic sulfur compounds and methods for their production
KR100399854B1 (ko)	2003-12-18	살절지동물성옥사디아진중간체
FI70895C (fi)	1986-10-27	Foerfarande foer framstaellning av vinkaminsyraestrar
US3378592A (en)	1968-04-16	Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide
US2483529A (en)	1949-10-04	Z-benzyl
SU539521A3 (ru)	1976-12-15	Способ получени аминоэфиров или их солей
US4244885A (en)	1981-01-13	α-Substituted-3-(halomethyl)-4-hydroxybenzeneacetic acids
SU897109A3 (ru)	1982-01-07	Способ получени сольватов цефалоспоринов
DK156221B (da)	1989-07-10	Fremgangsmaade til fremstilling af penicillansyre- og cephalosporansyrederivater
US4324903A (en)	1982-04-13	Malonic esters
KR830001969B1 (ko)	1983-09-29	6―｛D―(―) α-(4―에틸-2. 3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법
US4477677A (en)	1984-10-16	Process for the preparation of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid
US2517588A (en)	1950-08-08	Process for manufacture of penaldic acids and their derivatives
US3218338A (en)	1965-11-16	Method of making organic carbonating agents
SU545641A1 (ru)	1977-02-05	Способ получени эфиров бензимидазолил-1-уксусной кислоты или ее 2-замещенных
US2534332A (en)	1950-12-19	2-oxoimidazolines and process for preparing the same
SU487884A1 (ru)	1975-10-15	Способ получени 0-(ациламиноацил) -4-пиридинальдоксимов