CH501587A - Verfahren zur Herstellung von 2-substituierten 5-Chlorbenzophenonen - Google Patents

Verfahren zur Herstellung von 2-substituierten 5-Chlorbenzophenonen

Info

Publication number: CH501587A
Authority: CH; Switzerland
Prior art keywords: dependent; water; reduction; carried out; subclaims
Prior art date: 1968-03-20

Application number

CH1647668A

Other languages

German (de)

English (en)

Inventor

Wolfgang Dr Lugenheim

Hans-Joachim Dipl Che Heidrich

Original Assignee

Dresden Arzneimittel

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.)

1968-03-20

Filing date

1968-11-05

Publication date

1971-01-15

1968-11-05 Application filed by Dresden Arzneimittel filed Critical Dresden Arzneimittel

1971-01-15 Publication of CH501587A publication Critical patent/CH501587A/de

Links

239000003814 drug Substances 0.000 title abstract description 3
229940079593 drug Drugs 0.000 title abstract description 3
239000000543 intermediate Substances 0.000 title abstract description 3
CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical class ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 title 1
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
MUHJZJKVEQASGY-UHFFFAOYSA-N 5-chloro-3-phenyl-2,1-benzoxazole Chemical compound C=12C=C(Cl)C=CC2=NOC=1C1=CC=CC=C1 MUHJZJKVEQASGY-UHFFFAOYSA-N 0.000 claims description 9
-1 2-substituted 5 chlorobenzophenones Chemical class 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 6
238000006722 reduction reaction Methods 0.000 claims 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000007868 Raney catalyst Substances 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
229910000564 Raney nickel Inorganic materials 0.000 claims 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
238000010531 catalytic reduction reaction Methods 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
229910052718 tin Inorganic materials 0.000 claims 1
239000011135 tin Substances 0.000 claims 1
239000011701 zinc Substances 0.000 claims 1
229910052725 zinc Inorganic materials 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000000129 anionic group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000001188 haloalkyl group Chemical group 0.000 abstract 1
239000013067 intermediate product Substances 0.000 abstract 1
239000000203 mixture Substances 0.000 description 6
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
HPVUXGAKPJOZBW-UHFFFAOYSA-N [2-(benzylamino)-5-chlorophenyl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NCC1=CC=CC=C1 HPVUXGAKPJOZBW-UHFFFAOYSA-N 0.000 description 1
BASRYQBPQWFPEF-UHFFFAOYSA-N [5-chloro-2-(ethylamino)phenyl]-phenylmethanone Chemical compound CCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BASRYQBPQWFPEF-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WZTIKNRSYKDRQF-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WZTIKNRSYKDRQF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1647668A 1968-03-20 1968-11-05 Verfahren zur Herstellung von 2-substituierten 5-Chlorbenzophenonen CH501587A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD13094768		1968-03-20

Publications (1)

Publication Number	Publication Date
CH501587A true CH501587A (de)	1971-01-15

Family

ID=5479840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1647668A CH501587A (de)	1968-03-20	1968-11-05	Verfahren zur Herstellung von 2-substituierten 5-Chlorbenzophenonen

Country Status (2)

Country	Link
CH (1)	CH501587A (cs)
CS (1)	CS150240B2 (cs)

1968
- 1968-11-05 CH CH1647668A patent/CH501587A/de not_active IP Right Cessation
1969
- 1969-02-05 CS CS75169A patent/CS150240B2/cs unknown

Also Published As

Publication number	Publication date
CS150240B2 (cs)	1973-09-04

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Legal Events

Date	Code	Title	Description
1975-06-13	PL	Patent ceased