NO123806B - - Google Patents

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Info

Publication number: NO123806B
Authority: NO; Norway
Prior art keywords: formula; compound; lower alkyl; chlorine; chlorinating agent
Prior art date: 1968-06-04

Application number

NO2293/69A

Other languages

English (en)

Norwegian (no)

Inventor

Ning R Ye-Fong

L H Sternbach

Original Assignee

Hoffmann La Roche

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.)

1968-06-04

Filing date

1969-06-03

Publication date

1972-01-17

1969-06-03 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1972-01-17 Publication of NO123806B publication Critical patent/NO123806B/no

Links

150000001875 compounds Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 13
239000012320 chlorinating reagent Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
239000003054 catalyst Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
-1 alkyl hypochlorite Chemical compound 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
WHTNHYRHHHFFBV-UHFFFAOYSA-N ClNS(=O)=O Chemical class ClNS(=O)=O WHTNHYRHHHFFBV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
FVZCUXZVWHLKAR-UHFFFAOYSA-N OS(O)(=O)=S.I Chemical compound OS(O)(=O)=S.I FVZCUXZVWHLKAR-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
JNWGYSUVTQLCQP-UHFFFAOYSA-N n-chloro-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NCl JNWGYSUVTQLCQP-UHFFFAOYSA-N 0.000 description 1
HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002976 peresters Chemical class 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000007306 turnover Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO2293/69A 1968-06-04 1969-06-03 NO123806B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US73421668A	1968-06-04	1968-06-04

Publications (1)

Publication Number	Publication Date
NO123806B true NO123806B (de)	1972-01-17

Family

ID=24950764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO2293/69A NO123806B (de)	1968-06-04	1969-06-03

Country Status (11)

Country	Link
US (1)	US3635948A (de)
AT (1)	AT286304B (de)
CH (1)	CH511865A (de)
CS (1)	CS155204B2 (de)
ES (1)	ES367983A1 (de)
FI (1)	FI49168C (de)
HU (1)	HU162253B (de)
NL (1)	NL163784C (de)
NO (1)	NO123806B (de)
SE (1)	SE372268B (de)
YU (1)	YU34204B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1333502A (en) *	1971-03-05	1973-10-10	Ravizza Spa	Process for the preparation of a 7-chlorobenzodiazepine
GB1333501A (en) *	1971-03-05	1973-10-10	Ravizza Spa	Process for the preparation of 7-chlorobenzodiazepine de rivatives

1968
- 1968-06-04 US US734216A patent/US3635948A/en not_active Expired - Lifetime
1969
- 1969-05-12 CH CH720269A patent/CH511865A/de not_active IP Right Cessation
- 1969-06-02 YU YU1370/69A patent/YU34204B/xx unknown
- 1969-06-02 FI FI691648A patent/FI49168C/fi active
- 1969-06-03 NO NO2293/69A patent/NO123806B/no unknown
- 1969-06-03 ES ES367983A patent/ES367983A1/es not_active Expired
- 1969-06-03 HU HUHO1179A patent/HU162253B/hu unknown
- 1969-06-03 AT AT527369A patent/AT286304B/de not_active IP Right Cessation
- 1969-06-04 NL NL6908475.A patent/NL163784C/xx not_active IP Right Cessation
- 1969-06-04 SE SE6907904A patent/SE372268B/xx unknown
- 1969-06-04 CS CS397269A patent/CS155204B2/cs unknown

Also Published As

Publication number	Publication date
AT286304B (de)	1970-12-10
FI49168C (fi)	1975-04-10
HU162253B (de)	1973-01-29
NL163784C (nl)	1980-10-15
FI49168B (de)	1974-12-31
NL163784B (nl)	1980-05-16
SE372268B (de)	1974-12-16
CH511865A (de)	1971-08-31
NL6908475A (de)	1969-12-08
US3635948A (en)	1972-01-18
ES367983A1 (es)	1971-05-01
YU137069A (en)	1978-06-30
CS155204B2 (de)	1974-05-30
YU34204B (en)	1979-02-28

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Elliott et al.	1980	Hydrazides and thiohydrazides as sources of condensed oxadiazines and thiadiazines, including novel azo derivatives based on dithizone
Nishiwaki	1966	5-Halogenopyrimidines—IV: Extension on the nature of pyrimidine substrates and the kind of N-halogenosuccinimides
JP4028021B2 (ja)	2007-12-26	非対称性４，６−ビス（アリールオキシ）ピリミジン化合物の製造方法
Boulton et al.	1966	A new benzofurazan synthesis
US4221746A (en)	1980-09-09	Preparation of hexanitrostilbene
US3042684A (en)	1962-07-03	J-ethtl-jj-nitrovinylindole
Robinson et al.	1932	42. Experiments on the synthesis of physostigmine (eserine). Part II. Synthesis of a base which is believed to be dl-noreserethole
Giori et al.	1986	Reactivity of pyrazolo [4, 3‐c][1, 2, 5] oxadiazin‐3 (5H)‐ones toward C‐nucleophiles: Synthesis of pyrazolo [3, 4‐b] pyrazines
Bhat et al.	1979	Photooxygenation of aziridines and some potential azomethine ylides
Russell et al.	1996	8-Endo versus 5-exo cyclization of unsaturated acrylate esters upon reaction with t-BuHgI/KI
Yoneda et al.	1981	Reactivity of 4a, 5-epoxy-5-deazaflavins
Itai et al.	1962	Potential Anti-cancer Agents. IV. 3-Substituted 6-Chloropyridazine 1-Oxides
US4412957A (en)	1983-11-01	Process for preparing dialkyl propanediimidate dihydrohalides
Kaji et al.	1984	The synthesis of pyrazolo [3, 4‐d] pyridazines. Photochemical cyclization to pyrazolo [3, 4‐d] pyridazin‐4 (5H)‐ones with subsequent functionalization
Tókés et al.	1991	Bromo-derivatives of 2′-NHR-3, 4-Methylenedioxychalcone and its 4-Quinolone Isomer
NO138849B (no)	1978-08-14	Fremgangsmaate til fremstilling av 2-alkoksy-1,4-benzodiazepinderivater
Wilbert et al.	1957	Improved Synthesis of 4-Ethylpyridine
Nakanishi et al.	1983	Synthesis of imidazole derivatives from α-halooximes and amidines by use of iron carbonyls
Bahner et al.	1962	3, 4-Dihydroxyphenacyl Chloride Quaternary Salts of Heterocyclic Nitrogen Compounds1