KR950014065A - 알킬술피닐벤즈아미드류 및 1, 2-벤즈이소티아졸-3-온류의 제조방법 - Google Patents
알킬술피닐벤즈아미드류 및 1, 2-벤즈이소티아졸-3-온류의 제조방법 Download PDFInfo
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- KR950014065A KR950014065A KR1019940031079A KR19940031079A KR950014065A KR 950014065 A KR950014065 A KR 950014065A KR 1019940031079 A KR1019940031079 A KR 1019940031079A KR 19940031079 A KR19940031079 A KR 19940031079A KR 950014065 A KR950014065 A KR 950014065A
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- Prior art keywords
- benzamide
- methylthio
- group
- general formula
- phenyl
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- 238000004519 manufacturing process Methods 0.000 title claims abstract 7
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical class C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 title claims abstract 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract 12
- 239000002904 solvent Substances 0.000 claims abstract 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 230000002140 halogenating effect Effects 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- MHSFQLRSHXSBDJ-UHFFFAOYSA-N 2-methylsulfanyl-n-phenylbenzamide Chemical compound CSC1=CC=CC=C1C(=O)NC1=CC=CC=C1 MHSFQLRSHXSBDJ-UHFFFAOYSA-N 0.000 claims 2
- HSOQDPYTTOKEHI-UHFFFAOYSA-N 2-methylsulfanylbenzamide Chemical compound CSC1=CC=CC=C1C(N)=O HSOQDPYTTOKEHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- -1 methoxyphenyl Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- BHHGABOCAHPYMA-UHFFFAOYSA-N 2-bromo-N-phenylbenzamide Chemical compound BrC1=CC=CC=C1C(=O)NC1=CC=CC=C1 BHHGABOCAHPYMA-UHFFFAOYSA-N 0.000 claims 1
- IXEXZRWRTPMQBQ-UHFFFAOYSA-N 2-bromo-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=CC=C1Br IXEXZRWRTPMQBQ-UHFFFAOYSA-N 0.000 claims 1
- DWCBZUWYUAIEEP-UHFFFAOYSA-N 2-bromo-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1Br DWCBZUWYUAIEEP-UHFFFAOYSA-N 0.000 claims 1
- NHNAEZDWNCRWRW-UHFFFAOYSA-N 2-bromobenzamide Chemical compound NC(=O)C1=CC=CC=C1Br NHNAEZDWNCRWRW-UHFFFAOYSA-N 0.000 claims 1
- NKUJXBPYWPGLBA-UHFFFAOYSA-N 2-chloro-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=CC=C1Cl NKUJXBPYWPGLBA-UHFFFAOYSA-N 0.000 claims 1
- OUMQNCAKBPDGIY-UHFFFAOYSA-N 2-chloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1Cl OUMQNCAKBPDGIY-UHFFFAOYSA-N 0.000 claims 1
- AXQVIWHAEYLGLO-UHFFFAOYSA-N 2-chloro-n-phenylbenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=CC=CC=C1 AXQVIWHAEYLGLO-UHFFFAOYSA-N 0.000 claims 1
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 claims 1
- DEFUMLHLEJNWIO-UHFFFAOYSA-N 2-methylbenzenecarbothioamide Chemical compound CC1=CC=CC=C1C(N)=S DEFUMLHLEJNWIO-UHFFFAOYSA-N 0.000 claims 1
- AGQQRYAOOAHDON-UHFFFAOYSA-N 2-methylsulfanyl-3-nitro-n-phenylbenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(SC)=C1C(=O)NC1=CC=CC=C1 AGQQRYAOOAHDON-UHFFFAOYSA-N 0.000 claims 1
- BPAPEFAWHVIDNI-UHFFFAOYSA-N 2-methylsulfinyl-n-phenylbenzamide Chemical compound CS(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 BPAPEFAWHVIDNI-UHFFFAOYSA-N 0.000 claims 1
- IPNCCSOWAWOQAL-UHFFFAOYSA-N 2-methylsulfinylbenzamide Chemical compound CS(=O)C1=CC=CC=C1C(N)=O IPNCCSOWAWOQAL-UHFFFAOYSA-N 0.000 claims 1
- OJFBXPPGXZYTDJ-UHFFFAOYSA-N 4-bromo-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=C(Br)C=C1 OJFBXPPGXZYTDJ-UHFFFAOYSA-N 0.000 claims 1
- JXFKDGIMTQHLIT-UHFFFAOYSA-N 4-bromo-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=C(Br)C=C1 JXFKDGIMTQHLIT-UHFFFAOYSA-N 0.000 claims 1
- QVTGXXQAVWWJRO-UHFFFAOYSA-N 4-bromo-n-phenylbenzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=CC=CC=C1 QVTGXXQAVWWJRO-UHFFFAOYSA-N 0.000 claims 1
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 claims 1
- IKOQAZLFSPOYRG-UHFFFAOYSA-N 4-chloro-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 IKOQAZLFSPOYRG-UHFFFAOYSA-N 0.000 claims 1
- TXRYLYLDCHDRSJ-UHFFFAOYSA-N 4-chloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=C(Cl)C=C1 TXRYLYLDCHDRSJ-UHFFFAOYSA-N 0.000 claims 1
- SFHDVPIEJXCMBP-UHFFFAOYSA-N 4-chloro-n-phenylbenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC=CC=C1 SFHDVPIEJXCMBP-UHFFFAOYSA-N 0.000 claims 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- XHSVHJUCHGPMIP-UHFFFAOYSA-N N-ethylsulfinylbenzamide Chemical compound C(C1=CC=CC=C1)(=O)NS(=O)CC XHSVHJUCHGPMIP-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- WOXHUORDHZSLBI-UHFFFAOYSA-N n-(4-chlorophenyl)-2-methylsulfanylbenzamide Chemical compound CSC1=CC=CC=C1C(=O)NC1=CC=C(Cl)C=C1 WOXHUORDHZSLBI-UHFFFAOYSA-N 0.000 claims 1
- PUIYIJWJYXUFGR-UHFFFAOYSA-N n-benzyl-2-bromobenzamide Chemical compound BrC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 PUIYIJWJYXUFGR-UHFFFAOYSA-N 0.000 claims 1
- XZGDVGQQACMHDH-UHFFFAOYSA-N n-benzyl-2-chlorobenzamide Chemical compound ClC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 XZGDVGQQACMHDH-UHFFFAOYSA-N 0.000 claims 1
- MQEROOKYQPHGHZ-UHFFFAOYSA-N n-benzyl-2-methylsulfanylbenzamide Chemical compound CSC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 MQEROOKYQPHGHZ-UHFFFAOYSA-N 0.000 claims 1
- RLXPLHLLCIBNAN-UHFFFAOYSA-N n-benzyl-4-bromobenzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NCC1=CC=CC=C1 RLXPLHLLCIBNAN-UHFFFAOYSA-N 0.000 claims 1
- LSMWDKIFKGLNSW-UHFFFAOYSA-N n-benzyl-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC=C1 LSMWDKIFKGLNSW-UHFFFAOYSA-N 0.000 claims 1
- LFMNJMFZGDAIFX-UHFFFAOYSA-N n-cyclohexyl-2-methylsulfanylbenzamide Chemical compound CSC1=CC=CC=C1C(=O)NC1CCCCC1 LFMNJMFZGDAIFX-UHFFFAOYSA-N 0.000 claims 1
- DRNYXRUKJRFDNH-UHFFFAOYSA-N n-ethyl-2-ethylsulfanylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1SCC DRNYXRUKJRFDNH-UHFFFAOYSA-N 0.000 claims 1
- KMKSGPDJZFWEBL-UHFFFAOYSA-N n-ethyl-2-methylsulfanylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1SC KMKSGPDJZFWEBL-UHFFFAOYSA-N 0.000 claims 1
- PWBWOJDNAURSGN-UHFFFAOYSA-N n-ethyl-2-methylsulfinylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1S(C)=O PWBWOJDNAURSGN-UHFFFAOYSA-N 0.000 claims 1
- ISVPSMUHTLLCNT-UHFFFAOYSA-N n-sulfinylbenzamide Chemical compound O=S=NC(=O)C1=CC=CC=C1 ISVPSMUHTLLCNT-UHFFFAOYSA-N 0.000 claims 1
- FDZWAQZTLVREEF-UHFFFAOYSA-N n-tert-butylsulfanylbenzamide Chemical compound CC(C)(C)SNC(=O)C1=CC=CC=C1 FDZWAQZTLVREEF-UHFFFAOYSA-N 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 150000004714 phosphonium salts Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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- C07C2601/14—The ring being saturated
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Abstract
할로벤즈아미드를 염기의 존재하의 불균일 용매에서 알칸티올과 반응시키는 알칼티오벤즈아미드의 제조 방법;알칼티오벤젠아미드를 불균일 용매에서 할로겐과 반응시키는 알킬술피닐벤즈아미드의 제조 방법;할로즈아미드를 염기의 존재하에서, 불균일 용매에서 할로겐과 반응시키는 알킬술피닐벤즈아미드의 제조 방법;및 2-(알킬티오)벤즈아미드를 할로겐화제와 반응시키는 1, 2-벤즈이소티아졸-3-온의 제조 방법.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 하기 일반식(I)의 할로벤즈아미드를 하기 일반식(Ⅱ)의 알칸티올과 염기 존재하에 불균일 용매에서 반응시켜서 하기 일반식(Ⅲ)의 알킬티오벤즈아미드를 수득하는 것을 특징으로 하는 일반식(Ⅲ)의 알킬티오벤즈아미드의 제조 방법:(상기식에서, X는 Cl 또는 Br을 나타내고 R1은 수소원자 또는 C1-4의 알킬기, 아릴기 또는 아르아킬기를 나타내고, R2는 C1-4의 알킬기를 나타낸다. ).
- 제1항에 있어서, 반응을 상전이 촉매의 존재하에서 수행하는 방법.
- 제2항에 있어서, 상전이 촉매가 4차 암모늄염 및 4차 포스포늄염으로 구성된 군으로 부터 선택되는 방법.
- 제1항에 있어서, 일반식(I)의 화합물이 2-클로로벤즈아미드, N-에틸-2-클로로벤즈아미드, N- 페닐-2-클로로벤즈아미드, N-4-톨릴-2-클로로벤즈아미드, N - 벤질 -2-클로로벤즈아미드, 2- 브로모벤즈아미 드, N-에 틸 -2-브로모벤즈아미 드, N-페 닐-2-브로모벤즈아미드, N-4-톨릴 -2-브로모벤즈아미드, N -벤질 -2-브로모벤즈아미드, 4-클로로벤즈아미드, N-에 틸 -4-클로로벤즈아미드, N-페 닐-4-클로로벤즈아미드, N-4-톨릴 -4-클로로벤즈아미드, N - 벤질 -4-클로로벤즈아미드, 4 -브로모벤즈아미드, N-에 틸 -4-브로모벤즈아미드, N-페 닐-4-브로모벤즈아미드,N -4-톨릴 -4-브로모벤즈아미드 및 N-벤질-4-브로모벤즈아미드로 구성된 군으로 부터 선택된 화합물인 방법.
- 제1항에 있어서, 일반식(Ⅲ)의 화합물이 2-(메틸티오)벤즈아미드 또는 N-페닐-2-(메틸티오) 벤즈아미드인 방법
- 제1항에 있어서, 염기가 알칼리 금속 히드록시드인 방법.
- 하기 일반식(Ⅲ)의 알킬티오벤즈아미드를 할로겐과 불균일 용매에서 반응시켜서 하기 일반식(Ⅳ)의 알킬술피닐벤즈아미드를 수득하는 것을 특징으로하는 일반식(Ⅳ)의 알킬술피닐벤즈아미드의 제조 방법.(상기식에서, R1은 수소 원자, 또는 C1-4의 알킬기, 아릴기 또는 아르알킬기를 나타내고, R2는 C1-4의 알킬기를 나타낸다.).
- 제7항에 있어서, 일반식(Ⅳ)의 화합물이 2-(메틸술피닐)벤즈아미드, 2-(에틸술피닐)벤즈아미드, 2- (n-프로필술피닐)벤즈아미드, 2- (이소프로필술피닐)벤즈아미드, 2- (n-부틸술피닐)벤즈아미드, 2- (이소부틸술피닐)벤즈아미 드, 2- (5-부틸술피닐)벤즈아미드, 2- (t-부틸술피닐)벤즈아미드, N-에틸 -2- (메틸술피닐)벤즈아미드, N-페닐 -2- (메틸술피닐)벤즈아미드, N -4-톨릴-2- (메틸술피닐)벤즈아미드, N- 벤질 -2- (메틸술피닐)벤즈아미드, N-에 틸 -2- (에틸술피닐)벤즈아미드, N-페닐-2- (에틸술피닐)벤즈아미드, N-4-톨릴 -2- (에틸술피닐)벤즈아미드, N-벤질 -2- (에틸술피닐)벤즈아미드, 4- (메틸술피닐)벤즈아미드, N- (에틸술피닐)벤즈아미드, N-에 틸 -4- (메틸술피닐)벤즈아미드, N-페 닐 -4- (메틸술필닐)벤즈아미드, N-4-톨릴 -4- (메틸술피닐)벤즈아미드 및 N-벤질-4- (메틸술피닐)벤즈아미드로 구성된 군으로 부터 선택되는 방법.
- 하기 일반식(I)의 할로벤즈아미드를 하기 일반식(Ⅱ)의 알칸올과 염기 존재하에 불균일 용매에서 반응시키고;상기 반응 흔합물에 할로겐을 첨가하여 더 반응시켜서 하기 일반식(Ⅳ)의 알킬술피닐벤즈아미드를 수득하는 것을 특징으로하는 일반식(Ⅳ)의 알킬술피닐벤즈아미드를 제조하는 방법:(상기식에서, X는 Cl 또는 Br이고, R'은 수소 원자, 또는 C1-4의 알킬기, 아릴기 또는 아르알킬기를 나타내고, R2는 C1-4의 알킬기를 나타낸다. ).
- 제9항에 있어서, 반응을 톨루엔 및 물로 구성된 불균일 용매에서 원-포트 (one-pot)로 수행하는 방법.
- 하기 일반식(Ⅴ)의 2-(알킬티오)벤즈아미드를 할로겐화제와 반응시켜서 하기 일반식(Ⅵ)의 1, 2-벤즈이소티아졸-3-온을 수득하는 것을 특징으로하는 일반식(Ⅵ)의 1, 2-벤즈이소티아졸-3-온의 제조 방법 .(상기식에서, R3는 수소 원자, 또는 C1-12의 직쇄 또는 분지쇄 알킬기, 시클로알킬기, 아릴기, 또는 아르알킬기를 나타내고;R4는 C1-4의 알킬기를 나타내고;R5는 수소 원자, C1-4의 알킬기, C1-4의 알콕시기, 니트로기, 카르복실기 또는 그의 에스테르, 또는 할로겐 원자를 나타낸다).
- 제11항에 있어서, 할로겐화제가 하기 일반식(Ⅶ)의 술푸릴할라이드, 포스포러스 펜타클로라이드, 포스포러스 트리글로라이드, 및 염소로 구성된 군으로부터 선택되는 방법:SO2X2(Ⅶ)(상기식에서, X는 Cl 또는 Br이다. ).
- 제11항에 있어서, 일반식(Ⅴ)의 화합물이 2-(메틸티오)벤즈아미드, 2-(에틸티오)벤즈아미드, 2(t-부틸티오)벤즈아미드, N -에틸 -2- (메틸티오)벤즈아미드, N -에 틸 -2- (에틸티오)벤즈아미드, N-이 소프로필 -2- (메틸티오)벤즈아미드, N- (t-부틸 ) -2- (메틸티오)벤즈아미드, N -헥실-2- (메틸티오)벤즈아미드, N-옥틸 -2- (메틸티오)벤즈아미드, N- 데실 -2- (메틸티오)벤즈아미드, N-도데실 -2- (메틸티오)벤즈아미드, N-시클로헥실 -2- (메틸티오)벤즈아미드, N-페닐-2- (메틸티오)벤즈 아미드, N- (4-톨릴) -2- (메틸티오)벤즈아미 드, N- 4-(메톡시페닐) -2- (메틸티오)벤즈아미드, N-(4-클로로페닐) -2- (메틸티오)벤즈아미드, N - (1-나프틸) -2- (메틸티오)벤즈아미드, N-벤질 -2-(메틸티오)벤즈아미드, N - 벤질 -2- (프로필티오)벤즈아미드, N-벤질 -2- (부틸티오)벤즈아미드, N-페닐-3-메틸 -2- (메틸티오)벤즈아미드, N -메틸 -5-부틸 -2- (메틸티오)벤즈아미드, N-부틸 -4-메톡시 -2- (메틸티오)벤즈아미 드, N -페닐-2-메틸티오-3-니트로벤즈아미드, 4-클로로-2- (메 틸티오)벤즈아미드, 4-카르복시 -2- (메틸티오)벤즈아미드 및 4-메톡시카르보닐 -2- (메틸티오)벤즈아미드로 구성된 군으로 부터 선택되는 방법.
- 제11항에 있어서, 일반식(Ⅴ)의 2-(알킬티오)벤즈아미드가 일반식(Ⅷ)의 할로벤즈아미드를 하기 일반식(Ⅸ)의 알칸티올과 염기의 존재하에, 불균일 용매에서, 반응시켜서 수득되는 방법:(상기식에서, S는 Cl 또는 Br이고,R3은 수소 원자, 또는 C1-12의 직쇄 또는 분지쇄의 알킬기, 시클로알킬기, 아릴기 또는 아르알킬기를 나타내고;R4는 C1-4의 알킬기를 나타내고:R5는 수소 원자, C1-4의 알킬기, C1-4의 알콕시기, 니트로기, 카르복실기 또는 그의 에스테르, 또는 할로겐원자를 나타낸다.).※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| JP31917993A JP3373271B2 (ja) | 1993-11-24 | 1993-11-24 | アルキルチオベンズアミド類の製造方法 |
| JP35093293A JP3495072B2 (ja) | 1993-12-29 | 1993-12-29 | １，２−ベンズイソチアゾール−３−オン類の製造方法 |
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| BRPI0912383A2 (pt) | 2008-05-08 | 2015-07-28 | Basf Se | Processo para preparar aril carboxamidas |
| CN102241616A (zh) * | 2010-05-12 | 2011-11-16 | 利尔化学股份有限公司 | 砜的制备方法 |
| CN103145638B (zh) * | 2013-03-18 | 2015-05-27 | 上海添蓝生物科技有限公司 | 2-丁基-1,2-苯并异噻唑啉-3-酮(bbit)的制备新方法 |
| PL3070076T3 (pl) * | 2013-11-12 | 2022-05-09 | Nihon Nohyaku Co., Ltd. | Związki amidowe lub ich sole, oraz ich zastosowanie jako rolnicze i ogrodnicze środki bakteriobójcze |
| CN103755605B (zh) * | 2013-12-30 | 2016-08-17 | 中国科学院上海硅酸盐研究所 | 对己硫基苯甲醛的制备方法 |
| CN103694194A (zh) * | 2014-01-04 | 2014-04-02 | 寿光新泰精细化工有限公司 | 一种2-甲基-1,2-苯并异噻唑啉-3-酮的合成方法 |
| CN103664817A (zh) * | 2014-01-04 | 2014-03-26 | 寿光新泰精细化工有限公司 | 一种2-丁基-1,2-苯并异噻唑啉-3-酮的合成方法 |
| CN105646300B (zh) * | 2016-01-25 | 2017-11-10 | 黑龙江八一农垦大学 | 一种2‑辛亚砜‑1,4‑萘醌的制备方法 |
| CN105753805A (zh) * | 2016-03-31 | 2016-07-13 | 寿光新泰精细化工有限公司 | 一种1,2-苯并异噻唑-3-酮的提纯方法 |
| CN105801516B (zh) * | 2016-04-28 | 2018-05-04 | 大丰跃龙化学有限公司 | 一种1,2-苯并异噻唑啉-3-酮提纯工艺 |
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| DE3500577A1 (de) * | 1985-01-10 | 1986-07-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,2-benzisothiazolonen |
| FR2583046B1 (fr) * | 1985-06-05 | 1987-07-17 | Cird | Alkyl ou aralkyl thio-2 cycloalkene-1 carboxamides-1 et leurs sulfoxydes, leurs procedes de preparation et leur application a la synthese de tri et tetramethylene-4,5 isothiazoline-4, ones-3 |
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Also Published As
| Publication number | Publication date |
|---|---|
| DE69404615T2 (de) | 1997-12-04 |
| CA2136167C (en) | 2005-08-02 |
| US5508416A (en) | 1996-04-16 |
| DE69404615D1 (de) | 1997-09-04 |
| EP0751123A3 (en) | 1997-01-15 |
| TW402585B (en) | 2000-08-21 |
| KR100219893B1 (ko) | 1999-09-01 |
| EP0751123A2 (en) | 1997-01-02 |
| EP0751123B1 (en) | 2000-05-10 |
| US5672751A (en) | 1997-09-30 |
| DE69424446D1 (de) | 2000-06-15 |
| CN1107837A (zh) | 1995-09-06 |
| EP0657438A2 (en) | 1995-06-14 |
| CN1042530C (zh) | 1999-03-17 |
| US5744609A (en) | 1998-04-28 |
| EP0657438B1 (en) | 1997-07-30 |
| CN1215722A (zh) | 1999-05-05 |
| CN1215721A (zh) | 1999-05-05 |
| CA2136167A1 (en) | 1995-05-25 |
| CN1086693C (zh) | 2002-06-26 |
| EP0657438A3 (en) | 1995-10-11 |
| DE69424446T2 (de) | 2000-08-24 |
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