NO148415B - INTERMEDIATE FOR USE IN PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METHYLYCYLOHEXYLAMINE - Google Patents
INTERMEDIATE FOR USE IN PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METHYLYCYLOHEXYLAMINEInfo
- Publication number
- NO148415B NO148415B NO823977A NO823977A NO148415B NO 148415 B NO148415 B NO 148415B NO 823977 A NO823977 A NO 823977A NO 823977 A NO823977 A NO 823977A NO 148415 B NO148415 B NO 148415B
- Authority
- NO
- Norway
- Prior art keywords
- amino
- bromhexine
- preparation
- methylycylohexylamine
- dibrombenzyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 2-AMINO-3,5-DIBROMBENZYL Chemical class 0.000 title description 3
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 claims description 10
- RQJFMNQNCRVVFJ-UHFFFAOYSA-N 6,8-dibromo-1,4-dihydro-3,1-benzoxazin-2-one Chemical group N1C(=O)OCC2=CC(Br)=CC(Br)=C21 RQJFMNQNCRVVFJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960003870 bromhexine Drugs 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000012434 nucleophilic reagent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229960002335 bromhexine hydrochloride Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YRSGDLIATOURQO-UHFFFAOYSA-N ethyl 4-acetyl-5-oxohexanoate Chemical compound CCOC(=O)CCC(C(C)=O)C(C)=O YRSGDLIATOURQO-UHFFFAOYSA-N 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Foreliggende oppfinnelse vedrører en hittil ukjent forbindelse The present invention relates to a hitherto unknown compound
som kan anvendes som et mellomprodukt ved fremstilling av N-(2-amino-3,5-dibrombenzyl)-N-metylcykloheksylamin med tri-vialnavnet bromheksin og med formelen: which can be used as an intermediate in the production of N-(2-amino-3,5-dibromobenzyl)-N-methylcyclohexylamine with the trivial name bromhexine and with the formula:
som er en kjent forbindelse med verdifulle farmakologiske egenskaper i form av slimløsende og hostestillende virkninger. which is a known compound with valuable pharmacological properties in the form of expectorant and antitussive effects.
Bromheksin fremstilles som regel ved omsetning av et 2-amino-3,5-dibrombenzylderivat med N-metylcykloheksylamin eller et reaktivt derivat av dette amin, men de kjente fremstillings-måter av denne type har ulemper, f.eks. i form av vanskelig tilgjengelige utgangsmaterialer eller nødvendigheten av å Bromhexine is usually produced by reacting a 2-amino-3,5-dibromobenzyl derivative with N-methylcyclohexylamine or a reactive derivative of this amine, but the known production methods of this type have disadvantages, e.g. in the form of hard-to-reach starting materials or the necessity to
benytte beskyttelsesgrupper som bevirker at det ikke kan opp- use protection groups which mean that it cannot
nås optimalt utbytte av sluttproduktet, eller at fremstill- optimal yield of the final product is reached, or that the manufacture
ingen er mindre økonomisk enn ønskelig. none is less economical than desirable.
Formålet med oppfinnelsen er å tilveiebringe et mellomprodukt The purpose of the invention is to provide an intermediate product
som lett kan fremstilles i høyt utbytte og fra hvilke bromheksin også lett kan fremstilles i høyt utbytte. which can be easily prepared in high yield and from which bromhexine can also be easily prepared in high yield.
Det angjeldende mellomprodukt er ifølge oppfinnelsen 6,8-dibrom-1,4-dihydro-2H-3,l-benzoksazin-2-on med formelen: According to the invention, the intermediate in question is 6,8-dibromo-1,4-dihydro-2H-3,1-benzoxazin-2-one with the formula:
Det er et hvitt, krystallinsk stoff med smeltepunkt 218- It is a white, crystalline substance with a melting point of 218-
220°C, og det fremstilles lett i et utbytte på opptil 90% 220°C, and it is easily produced in a yield of up to 90%
fra det kjente 1,4-dihydro-2H-3,l-benzoksazin-2-on ved brom-ering. from the known 1,4-dihydro-2H-3,1-benzoxazin-2-one by bromination.
Ved oppvarming med N-metylcykloheksylamin gir dette mellomprodukt bromheksin direkte. Omsetningen foretas hensikts-messig under anvendelse av heksametylfosforsyretriamid som oppløsningsmiddel, og bromheksinet kan utvinnes fra reaksjonsblandingen som analytisk rent hydroklorid i et utbytte på ca. 9 0%. When heated with N-methylcyclohexylamine, this intermediate gives bromhexine directly. The reaction is conveniently carried out using hexamethylphosphoric acid triamide as solvent, and the bromhexine can be recovered from the reaction mixture as analytically pure hydrochloride in a yield of approx. 90%.
Den beskrevne omdannelse av mellomproduktet til bromheksin The described conversion of the intermediate to bromhexine
i høyt utbytte under enkle reaksjonsbetingelser er ytterst overraskende, fordi omsetninger av heterocykliske forbind-elser med nukleofile reagenser ifølge litteraturen kan føre til substitusjon på forskjellige steder i den heterocykliske gruppe, og det vil ikke kunne forutses om substitusjonen skjer på det ene eller det andre sted eller på flere steder. in high yield under simple reaction conditions is extremely surprising, because according to the literature, reactions of heterocyclic compounds with nucleophilic reagents can lead to substitution at different places in the heterocyclic group, and it will not be possible to predict whether the substitution takes place at one place or the other or in several places.
I et kjent oppslagsverk: "Advances in Heterocyclic Chemistry" fra 1979 angis dette direkte og belyses med flere eksempler. In a well-known reference work: "Advances in Heterocyclic Chemistry" from 1979, this is stated directly and illustrated with several examples.
Videre kan foreliggende mellomprodukt betraktes som en cyklisk uretanforbindelse, og om uretaner angis det like-ledes i "Comprehensive Organic Chemistry" fra 1979 at den for disse mest karakteristiske reaksjon er med nukleofile reagenser, idet det f.eks. ved erstatning av alkoksy- eller aryloksygruppen med et amin fås et ureaderivat eller en alko-hol, altså et helt annet sluttprodukt enn det som oppnås ved den ovenfor beskrevne omsetning. Furthermore, the present intermediate can be regarded as a cyclic urethane compound, and regarding urethanes it is also stated in "Comprehensive Organic Chemistry" from 1979 that the most characteristic reaction for these is with nucleophilic reagents, as it e.g. by replacing the alkoxy or aryloxy group with an amine, a urea derivative or an alcohol is obtained, i.e. a completely different end product than that obtained in the reaction described above.
Mellomproduktets fremstilling og anvendelse belyses ved nedenstående eksempel. The intermediate product's production and use is illustrated by the example below.
Eksempel Example
Til en oppløsning av 9,0 g (0,0604 mol) 1, 4-dihydro-2H-3 ,1-benzoksazin-2-on i 40 ml iseddik ble det tilsatt 60,9 g To a solution of 9.0 g (0.0604 mol) 1,4-dihydro-2H-3,1-benzoxazin-2-one in 40 ml of glacial acetic acid was added 60.9 g
(0,38 mol) brom, hvorved oppløsningens temperatur steg til 74°C. (0.38 mol) of bromine, whereupon the temperature of the solution rose to 74°C.
Oppløsningen ble hensatt for avkjøling og deretter helt i The solution was set aside to cool and then poured into
500 ml vann hvorved den bromerte benzoksazinon ble utfelt. Etter frafiltrering og vasking på filteret med vann, en for-tynnet oppløsning av surt natriumsulfitt og heksan i den angitte rekkefølge oppnådde man 6,8-dibrom-l,4-dihydro-2H-3,1-benzoksazin-2-on i et utbytte på 16,5 g (0,0537 mol) hvilket tilsvarer 89% av det teoretiske. Smeltepunktet var 218-220°C. 500 ml of water whereby the brominated benzoxazinone was precipitated. After filtering off and washing the filter with water, a dilute solution of acidic sodium sulphite and hexane in the order indicated, 6,8-dibromo-1,4-dihydro-2H-3,1-benzoxazin-2-one was obtained in a yield of 16.5 g (0.0537 mol), which corresponds to 89% of the theoretical. The melting point was 218-220°C.
Etter omkrystallisering fra etoksyetanol tilsatt aktivt karbon var stoffet analytisk rent. After recrystallization from ethoxyethanol with added active carbon, the substance was analytically pure.
Overskudd av brom kunne gjenvinnes fra modervæsken og vaske-vann ved destillasjon. Excess bromine could be recovered from the mother liquor and wash water by distillation.
For fremstilling av bromheksin, ble en blanding av 3,07 g (0,010 mol) av mellomproduktet og 4,52 g (0,040 mol) N-metylcykloheksylamin oppvarmet i 10 ml heksametylfosforsyretriamid under omrøring og tilbakeløpskjøling på et olje-bad med en temperatur på 210°c i 2 timer. Etter avkjøling ble reaksjonsblandingen helt i 70 ml vann og det ble tilsatt konsentrert saltsyre til sur reaksjon. Ved avkjøling i isvann under omrøring i en time ble hydrokloridet av bromheksin utkrystallisert. Det ble frafiltrert, vasket med vann og tørket. Dette ga 3,7 g (0,00897 mol) analytisk rent bromheksinhydroklorid med smeltepunkt 232-233,5°C, hvilket tilsvarer 89,7% av det teoretiske. For the preparation of bromhexine, a mixture of 3.07 g (0.010 mol) of the intermediate and 4.52 g (0.040 mol) of N-methylcyclohexylamine was heated in 10 ml of hexamethylphosphoric acid triamide with stirring and reflux in an oil bath at a temperature of 210 °c for 2 hours. After cooling, the reaction mixture was poured into 70 ml of water and concentrated hydrochloric acid was added for an acidic reaction. By cooling in ice water with stirring for one hour, the hydrochloride of bromhexine crystallized out. It was filtered off, washed with water and dried. This gave 3.7 g (0.00897 mol) of analytically pure bromhexine hydrochloride with a melting point of 232-233.5°C, which corresponds to 89.7% of the theoretical.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK230179A DK145718C (en) | 1979-06-01 | 1979-06-01 | DIBROME COMPOUND USE AS INTERMEDIATE IN THE PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METYLCYCLOHEXYLAMINE |
| DK230079A DK145714C (en) | 1979-06-01 | 1979-06-01 | METHOD FOR PREPARING N- (2-AMINO-3,5-DIBROMBENZYL) -N-METYLYCYLOHEXYLAMINE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO823977L NO823977L (en) | 1980-12-02 |
| NO148415B true NO148415B (en) | 1983-06-27 |
| NO148415C NO148415C (en) | 1983-10-12 |
Family
ID=26066477
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801617A NO148372C (en) | 1979-06-01 | 1980-05-30 | PROCEDURE FOR THE PREPARATION OF BROOM HEXINE |
| NO823977A NO148415C (en) | 1979-06-01 | 1982-11-26 | INTERMEDIATE FOR USE IN PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METHYLYCYLOHEXYLAMINE |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801617A NO148372C (en) | 1979-06-01 | 1980-05-30 | PROCEDURE FOR THE PREPARATION OF BROOM HEXINE |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT371800B (en) |
| CH (1) | CH642617A5 (en) |
| DE (1) | DE3020604A1 (en) |
| ES (1) | ES492005A0 (en) |
| FI (1) | FI68808C (en) |
| GB (1) | GB2053900B (en) |
| IE (1) | IE49820B1 (en) |
| KE (1) | KE3302A (en) |
| NL (1) | NL8003153A (en) |
| NO (2) | NO148372C (en) |
| SE (1) | SE433847B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2881955B1 (en) | 2005-02-11 | 2007-05-11 | Oreal | COSMETIC NANOEMULSION CONTAINING HYDROXYL UREA COMPOUND |
| CN102775316B (en) * | 2012-08-17 | 2013-06-12 | 夏智红 | Bromhexine hydrochloride compound and medicine composition thereof |
| CN102924295B (en) * | 2012-10-09 | 2014-10-29 | 石家庄东方药业有限公司 | Bromhexine hydrochloride crystal as well as preparation method and application of crystal |
| CN103145564B (en) * | 2013-03-15 | 2014-06-18 | 湖北美林药业有限公司 | Bromhexine hydrochloride compound and pharmaceutical composition thereof |
-
1980
- 1980-05-23 IE IE1081/80A patent/IE49820B1/en unknown
- 1980-05-23 SE SE8003874A patent/SE433847B/en not_active IP Right Cessation
- 1980-05-27 FI FI801705A patent/FI68808C/en not_active IP Right Cessation
- 1980-05-29 GB GB8017619A patent/GB2053900B/en not_active Expired
- 1980-05-30 ES ES492005A patent/ES492005A0/en active Granted
- 1980-05-30 AT AT0288580A patent/AT371800B/en not_active IP Right Cessation
- 1980-05-30 NO NO801617A patent/NO148372C/en unknown
- 1980-05-30 CH CH423780A patent/CH642617A5/en not_active IP Right Cessation
- 1980-05-30 DE DE19803020604 patent/DE3020604A1/en not_active Withdrawn
- 1980-05-30 NL NL8003153A patent/NL8003153A/en not_active Application Discontinuation
-
1982
- 1982-11-26 NO NO823977A patent/NO148415C/en unknown
-
1983
- 1983-07-11 KE KE3302A patent/KE3302A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2053900B (en) | 1983-04-20 |
| IE801081L (en) | 1980-12-01 |
| NO148372B (en) | 1983-06-20 |
| NL8003153A (en) | 1980-12-03 |
| FI68808B (en) | 1985-07-31 |
| NO148372C (en) | 1983-09-28 |
| SE433847B (en) | 1984-06-18 |
| NO823977L (en) | 1980-12-02 |
| ATA288580A (en) | 1982-12-15 |
| GB2053900A (en) | 1981-02-11 |
| DE3020604A1 (en) | 1980-12-11 |
| FI68808C (en) | 1985-11-11 |
| ES8104185A1 (en) | 1981-04-01 |
| FI801705A (en) | 1980-12-02 |
| SE8003874L (en) | 1980-12-02 |
| CH642617A5 (en) | 1984-04-30 |
| ES492005A0 (en) | 1981-04-01 |
| NO801617L (en) | 1980-12-02 |
| AT371800B (en) | 1983-07-25 |
| KE3302A (en) | 1983-08-19 |
| IE49820B1 (en) | 1985-12-25 |
| NO148415C (en) | 1983-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Finnegan et al. | Preparation and isomerization of 5-alkylaminotetrazoles | |
| NO119798B (en) | ||
| Miller et al. | Some Analogs of Troeger's Base and Related Compounds1 | |
| NO742255L (en) | ||
| NO148415B (en) | INTERMEDIATE FOR USE IN PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METHYLYCYLOHEXYLAMINE | |
| WO2002060893A1 (en) | Method for carbamoylating alcohols | |
| NO148974B (en) | DIFFERENCE PRESSURE SENSITIVE AS CONTROL DEVICE. | |
| Kiang et al. | 268. The action of acyl cyanides on 2-and 1: 2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole | |
| NO137153B (en) | ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SULFAMOYL PHENYL PYRROLIDONES | |
| DK145718B (en) | Dibromo compound for use as an intermediate in preparing N-(2-amino-3,5-dibromobenzyl)-N-methylcyclohexylamine. | |
| US2739984A (en) | Tetra-substituted diamino alkanes | |
| TW202210486A (en) | Method for preparing glp-1 receptor agonist | |
| KR100368163B1 (en) | A process for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde | |
| US5091581A (en) | Process for the selective preparation of n-substituted 1,4-diamino-2-nitrobenzenes | |
| US2397391A (en) | Phenanthridine derivatives | |
| US4201722A (en) | Process for separating 4,4'-diaminodiphenylmethane | |
| JP2002155058A (en) | Method for producing 1-substituted hydratoin compound | |
| SU18745A1 (en) | Method for producing 4-substituted ureas | |
| Borrows et al. | S 44. The synthesis of thyroxine and related substances. Part III. The synthesis of thyroxine from 2: 6-dinitrodiphenyl ethers | |
| US2836592A (en) | Chloeination procedure | |
| Wright | The Decomposition of Dibutylchloramine | |
| DK145714B (en) | Process for preparing N-(2-amino-3,5-dibromobenzyl)-N- methylcyclohexylamine | |
| US2850530A (en) | Substituted urea compounds and processes for preparing the same | |
| US4235819A (en) | Process for isolating 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds from a crude, acid reaction mixture thereof | |
| CN117466762A (en) | Preparation method of 2-amino-3, 5-dichloro-N-methylbenzamide |