JPH0518816B2 - - Google Patents
Info
- Publication number
- JPH0518816B2 JPH0518816B2 JP20543989A JP20543989A JPH0518816B2 JP H0518816 B2 JPH0518816 B2 JP H0518816B2 JP 20543989 A JP20543989 A JP 20543989A JP 20543989 A JP20543989 A JP 20543989A JP H0518816 B2 JPH0518816 B2 JP H0518816B2
- Authority
- JP
- Japan
- Prior art keywords
- chloroform
- residue
- difluoro
- water
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 2,3-difluoro-6-nitrophenyl Chemical group 0.000 claims description 4
- CMXSFIQKWXLYDU-UHFFFAOYSA-N 1-(2,3-difluoro-6-nitrophenoxy)-3-methoxypropan-2-ol Chemical compound COCC(O)COC1=C(F)C(F)=CC=C1[N+]([O-])=O CMXSFIQKWXLYDU-UHFFFAOYSA-N 0.000 claims description 2
- HRUQKPXEKXZHBS-UHFFFAOYSA-N 1-(2,3-difluoro-6-nitrophenoxy)-3-methoxypropan-2-one Chemical compound COCC(=O)COC1=C(F)C(F)=CC=C1[N+]([O-])=O HRUQKPXEKXZHBS-UHFFFAOYSA-N 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229940125782 compound 2 Drugs 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000010446 mirabilite Substances 0.000 description 5
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- KEGOHDCHURMFKX-UHFFFAOYSA-N 2,3-difluoro-6-nitrophenol Chemical compound OC1=C(F)C(F)=CC=C1[N+]([O-])=O KEGOHDCHURMFKX-UHFFFAOYSA-N 0.000 description 1
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 1
- RROQSCBOBBLOOA-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 Chemical compound C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 RROQSCBOBBLOOA-UHFFFAOYSA-N 0.000 description 1
- BTLPSAWPCLZLCV-UHFFFAOYSA-N CCOC(=O)C1=CN2CCOc3cccc(C1)c23 Chemical compound CCOC(=O)C1=CN2CCOc3cccc(C1)c23 BTLPSAWPCLZLCV-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 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
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- BOSBRKBHTFSORJ-UHFFFAOYSA-N diethyl 2-[[7,8-difluoro-3-(methoxymethyl)-2,3-dihydro-1,4-benzoxazin-4-yl]methylidene]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)=CN1C(COC2=C1C=CC(=C2F)F)COC)=O BOSBRKBHTFSORJ-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20543989A JPH02152947A (ja) | 1989-08-08 | 1989-08-08 | ジフルオロフェノキシ化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20543989A JPH02152947A (ja) | 1989-08-08 | 1989-08-08 | ジフルオロフェノキシ化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57112040A Division JPS591489A (ja) | 1982-06-29 | 1982-06-29 | ピリドベンゾオキサジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02152947A JPH02152947A (ja) | 1990-06-12 |
| JPH0518816B2 true JPH0518816B2 (en, 2012) | 1993-03-15 |
Family
ID=16506895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20543989A Granted JPH02152947A (ja) | 1989-08-08 | 1989-08-08 | ジフルオロフェノキシ化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02152947A (en, 2012) |
-
1989
- 1989-08-08 JP JP20543989A patent/JPH02152947A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02152947A (ja) | 1990-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69937077T2 (de) | Zwischenprodukte für die Herstellung von Imidazo-Pyridin-Derivate | |
| JP2520549B2 (ja) | フルオロシクロプロピルアミノアクリル酸エステル誘導体 | |
| KR0125115B1 (ko) | (-)피페라진 벤즈옥사진 유도체의 제조방법 | |
| JPH0148911B2 (en, 2012) | ||
| JPH027314B2 (en, 2012) | ||
| KR900004145B1 (ko) | 트리사이클릭 화합물의 제조방법 | |
| JPS62252790A (ja) | ピリドベンゾオキサジン誘導体 | |
| JPH0518816B2 (en, 2012) | ||
| JPH0374671B2 (en, 2012) | ||
| JPH0116837B2 (en, 2012) | ||
| JPH0317838B2 (en, 2012) | ||
| CS202069B2 (en) | Method of preparing 2-/4-substituted piperazine-1-yl/-4-amino-6,7-dimethoxyquinazolines | |
| JPH0331710B2 (en, 2012) | ||
| WO2000015596A1 (fr) | Procede de preparation d'acides benzoiques fluores | |
| JPH07121931B2 (ja) | ベンゾ〔ｂ〕フラン誘導体 | |
| JPS585902B2 (ja) | β↓−ニトロスチレン誘導体 | |
| JPH04364185A (ja) | ピリドベンゾオキサジン誘導体 | |
| JP4055246B2 (ja) | ５−クロロ−６−（α−フルオロアルキル）−４−ピリミドン及びその製法 | |
| JPS6379874A (ja) | イソインド−ル誘導体 | |
| JPS6043067B2 (ja) | ２‐アルコキシインドリジン誘導体およびその製法 | |
| JPH0399079A (ja) | インドリジン誘導体 | |
| JPS61271292A (ja) | ３−フルオロメチル−ピリドベンゾオキサジン誘導体 | |
| JPS5823693A (ja) | イミダゾキノキザリン化合物類 | |
| JPH03120287A (ja) | チエノピラゾロピリジン誘導体 | |
| JPS6256154B2 (en, 2012) |