KR850004244A - 4-(2-페녹시에틸)-1,2,4-트리아졸론의 제법 - Google Patents
4-(2-페녹시에틸)-1,2,4-트리아졸론의 제법 Download PDFInfo
- Publication number
- KR850004244A KR850004244A KR1019840007553A KR840007553A KR850004244A KR 850004244 A KR850004244 A KR 850004244A KR 1019840007553 A KR1019840007553 A KR 1019840007553A KR 840007553 A KR840007553 A KR 840007553A KR 850004244 A KR850004244 A KR 850004244A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- phenoxyethyl
- amide
- formula
- anion
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 3
- JMPSKGFVYCJNFO-UHFFFAOYSA-N 4-(2-phenoxyethyl)-1h-1,2,4-triazol-5-one Chemical compound O=C1NN=CN1CCOC1=CC=CC=C1 JMPSKGFVYCJNFO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000001408 amides Chemical class 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 239000012190 activator Substances 0.000 claims 7
- 150000001450 anions Chemical group 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 3
- -1 carbazate ester Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 claims 2
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- LERXMGDFVFWGFQ-UHFFFAOYSA-N n-(2-phenoxyethyl)propanamide Chemical compound CCC(=O)NCCOC1=CC=CC=C1 LERXMGDFVFWGFQ-UHFFFAOYSA-N 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QNJSWVQHWIFPGY-UHFFFAOYSA-N hydrazinecarboxylic acid;hydrochloride Chemical compound Cl.NNC(O)=O QNJSWVQHWIFPGY-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 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 claims 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 페놀과 2-에틸-2-옥사졸린(V)를 반응시켜 산출한N-(2-페녹시에틸) 프로피온아미드(Ⅳ)를 하기 일반식(Ⅲ)의 이미도일 헬라이드 또는 에스테르 중간물질의 생산을 위해 티오닐 클로라이드, 티오닐브로마이드, 포스포터스 옥시클로라이드, 포스겐 도는 디메틸 설페이트등의 아미드 활성제와 반응시켜 화합물(Ⅳ)의 마이드 작용기를 활성화하고 상기 화합물(Ⅲ)을 분리시키지 않은 채로 그 생성물을 일반식 H2NNHCO2R의 카르바제이트 에스테르로 반응시켜 알킬[1-[(2-페녹시에틸)아민]프로필렌]하이드라진 카르복실레이트산 부가염(Ⅱ)을 출시키고 그 화합물(Ⅱ)를 유리염기 형태로 적합하게 열처리 함으로써 화합물(I)로 전환시키는 것을 특징으로 하는 5-에틸-4-(2-페녹시에틸)-2H-1,2,4-트리아졸-3(4H)은 (I)을 제조하는 방법.상기식(Ⅱ)와 (Ⅲ)에서 R은 저급(C1-C4)알킬이며, X는 음이온으로서, 사용된 아미드 활성제의 음이온에 해당하며, Y는 바람직하게는 할로겐 또는 알콕시기이다.
- 제1항에 있어서, 아미드 활성제가 포스겐인 것을 특징으로 하는 제조방법.
- 제1항에 있어서, 아미드 활성제가 포스포러스 옥시클로라이드인 것을 특징으로 하는 제조방법.
- 제1항에 있어서, 열처리가 적합한 불활성 유기 용매에서 유리염기 형태의 화합물(Ⅱ)을 환류시키는 것을 특징으로 하는 제조방법.
- 실시예들에서 설명한 방법에 의한 일반식(I)화합물의 제조방법.
- 일반식(I) 화합물이 제조되는 것을 특징으로 하는 방법.
- 페놀라 2-에틸-2-옥사졸린(V)를 반응시켜 산출된 N-(2-페녹시에틸)프로피온 아미드(Ⅳ)를 하기 일반식(Ⅲ)의 아미도일 헬라이드 또는 에스테르 중간물질의 생산을 위해 티오닐 클로라이드, 티오닐 브로마이드 포스포러스 옥시클로라이드, 포스겐 또는 디메틸 설페이트등의 아미드 활성제와 반응시켜 화합물(Ⅳ)의 아미드 작용기를 활성화하여 상기 화합물(Ⅲ)을 분리시키지 않은채로 그 생성물을 일반식 H2NNHCO2R의 카르바게이트 에스테르로 반응시켜 알칼[1-[(2-페녹시에틸)아민]프로필렌]하이드라진 카르복실레이트 산부가염(Ⅱ)를 산출시키는 것을 특징으로 하는 일반식(Ⅱ) 화합물 제조방법.상기 식들에서 R은 저급(C1-C4)알킬이며, X는 음이온으로서, 사용된 아미드 활성제의 음이온에 해당하며, Y는 바람직하게는 할로겐 또는 알콕시기이다.
- 일반식(Ⅱ) 화합물이 제조되는 것을 특징으로 하는 방법.상기 식에서 R은 저급(C1-C4)알킬, X는 음이온으로, 제조시 사용된 아미드 활성제의 음이온에 해당함.
- 에틸(1-(2-페녹시에틸)아미노)프로필리덴)하이드라진 카르복실레이트 또는 그것의 산 부가염 또는 메틸(1-(2-페녹시에틸)아미노)프로필리덴)하이드라진 카르복실레이트하이드로 클로라이드를 포함하여 일반식(Ⅱ)의 어떠한 화합물물이라도 생이되는 것을 특징으로 하는 방법.
- 실시예들에서 설명한 방법을 특징으로 하는 일반식(Ⅱ) 화합물의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55672783A | 1983-11-30 | 1983-11-30 | |
US556727 | 1983-11-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850004244A true KR850004244A (ko) | 1985-07-11 |
KR890000990B1 KR890000990B1 (ko) | 1989-04-15 |
Family
ID=24222593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840007553A KR890000990B1 (ko) | 1983-11-30 | 1984-11-30 | 4-(2-페녹시에틸)-1,2,4-트리아졸론 및 이의제법 |
Country Status (25)
Country | Link |
---|---|
JP (1) | JPS60132969A (ko) |
KR (1) | KR890000990B1 (ko) |
AT (1) | AT387571B (ko) |
AU (1) | AU576338B2 (ko) |
BE (1) | BE901165A (ko) |
CA (1) | CA1233826A (ko) |
CH (1) | CH663613A5 (ko) |
CY (2) | CY1472A (ko) |
DE (1) | DE3443820C2 (ko) |
DK (3) | DK159970C (ko) |
ES (2) | ES8609282A1 (ko) |
FI (1) | FI81785C (ko) |
FR (1) | FR2555582B1 (ko) |
GB (2) | GB2150567B (ko) |
GR (1) | GR81110B (ko) |
HK (2) | HK16289A (ko) |
IE (1) | IE74871B1 (ko) |
IT (1) | IT1178641B (ko) |
KE (1) | KE3852A (ko) |
LU (1) | LU85657A1 (ko) |
NL (1) | NL8403635A (ko) |
SE (3) | SE456993B (ko) |
SG (1) | SG80588G (ko) |
YU (2) | YU44721B (ko) |
ZA (1) | ZA849264B (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2182241C (en) * | 1996-07-29 | 2002-09-17 | Bo Lei | Methods for the manufacture of nefazodone |
DE19902960A1 (de) | 1999-01-26 | 2000-07-27 | Bayer Ag | Verfahren zur Herstellung von Methylcarbazat |
CA2356450C (en) | 2001-09-10 | 2003-11-25 | Brantford Chemicals Inc. | An improved process for the preparation of nefazodone hydrochloride |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1126882B (de) * | 1960-05-03 | 1962-04-05 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1,2,4-Triazolonen-(5) |
DE1545646B1 (de) * | 1965-12-15 | 1969-09-18 | Boehringer Sohn Ingelheim | 1,3-Dimethyl-4-(2',4'-dichlorphenyl)-1,2,4-triazolon-(5) und Verfahren zu dessen Herstellung |
US4338317A (en) * | 1981-03-16 | 1982-07-06 | Mead Johnson & Company | Phenoxyethyl-1,2,4,-triazol-3-one antidepressants |
US4487773A (en) * | 1981-03-16 | 1984-12-11 | Mead Johnson & Company | 1,2,4-Triazol-3-one antidepressants |
US4613600A (en) * | 1983-09-30 | 1986-09-23 | Mead Johnson & Company | Antidepressant 1,2,4-triazolone compounds |
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1984
- 1984-11-26 YU YU1998/84A patent/YU44721B/xx unknown
- 1984-11-27 ZA ZA849264A patent/ZA849264B/xx unknown
- 1984-11-27 FI FI844647A patent/FI81785C/fi active IP Right Grant
- 1984-11-29 SE SE8406045A patent/SE456993B/sv not_active IP Right Cessation
- 1984-11-29 DK DK567384A patent/DK159970C/da not_active IP Right Cessation
- 1984-11-29 CA CA000468894A patent/CA1233826A/en not_active Expired
- 1984-11-29 IT IT23808/84A patent/IT1178641B/it active
- 1984-11-29 FR FR8418173A patent/FR2555582B1/fr not_active Expired
- 1984-11-29 LU LU85657A patent/LU85657A1/xx unknown
- 1984-11-29 IE IE305984A patent/IE74871B1/en not_active IP Right Cessation
- 1984-11-29 GR GR81110A patent/GR81110B/el unknown
- 1984-11-29 ES ES538079A patent/ES8609282A1/es not_active Expired
- 1984-11-29 NL NL8403635A patent/NL8403635A/nl active Search and Examination
- 1984-11-29 CH CH5700/84A patent/CH663613A5/de not_active IP Right Cessation
- 1984-11-29 BE BE0/214083A patent/BE901165A/fr not_active IP Right Cessation
- 1984-11-30 AT AT0380884A patent/AT387571B/de not_active IP Right Cessation
- 1984-11-30 AU AU36092/84A patent/AU576338B2/en not_active Expired
- 1984-11-30 GB GB08430275A patent/GB2150567B/en not_active Expired
- 1984-11-30 KR KR1019840007553A patent/KR890000990B1/ko not_active IP Right Cessation
- 1984-11-30 JP JP59252083A patent/JPS60132969A/ja active Granted
- 1984-11-30 DE DE3443820A patent/DE3443820C2/de not_active Expired - Lifetime
-
1986
- 1986-03-31 ES ES553547A patent/ES8706320A1/es not_active Expired
- 1986-05-20 YU YU826/86A patent/YU45325B/xx unknown
-
1987
- 1987-02-02 GB GB08702275A patent/GB2185983B/en not_active Expired
-
1988
- 1988-04-15 SE SE8801409A patent/SE469894B/sv not_active IP Right Cessation
- 1988-04-15 SE SE8801408A patent/SE464025B/sv not_active IP Right Cessation
- 1988-11-30 SG SG805/88A patent/SG80588G/en unknown
- 1988-12-21 KE KE3852A patent/KE3852A/xx unknown
-
1989
- 1989-02-23 HK HK162/89A patent/HK16289A/xx not_active IP Right Cessation
- 1989-02-23 HK HK163/89A patent/HK16389A/xx not_active IP Right Cessation
- 1989-07-21 CY CY1472A patent/CY1472A/xx unknown
- 1989-07-21 CY CY1471A patent/CY1471A/xx unknown
-
1990
- 1990-03-19 DK DK070790A patent/DK171451B1/da not_active IP Right Cessation
- 1990-03-19 DK DK070890A patent/DK70890D0/da not_active Application Discontinuation
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