JPS6160833B2 - - Google Patents

Info

Publication number: JPS6160833B2
Authority: JP; Japan
Prior art keywords: formula; parts; compound; benzoxazolone; aminophenol
Prior art date: 1979-03-09
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

Application number

JP2663079A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55120572A (en

Inventor

Junji Toda

Taiji Yamada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

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.)

1979-03-09

Filing date

1979-03-09

Publication date

1986-12-23

1979-03-09 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1979-03-09 Priority to JP2663079A priority Critical patent/JPS55120572A/ja

1980-09-17 Publication of JPS55120572A publication Critical patent/JPS55120572A/ja

1986-12-23 Publication of JPS6160833B2 publication Critical patent/JPS6160833B2/ja

Status Granted legal-status Critical Current

Links

ASSKVPFEZFQQNQ-UHFFFAOYSA-N Benzoxazolone Natural products C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 30
-1 benzoxazolone compound Chemical class 0.000 claims description 17
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
239000004202 carbamide Substances 0.000 claims description 13
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
229910017604 nitric acid Inorganic materials 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
238000006396 nitration reaction Methods 0.000 description 8
238000002844 melting Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
229910001873 dinitrogen Inorganic materials 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
JGYJZHYTADCWIK-UHFFFAOYSA-N 6-nitro-3h-1,3-benzoxazol-2-one Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)OC2=C1 JGYJZHYTADCWIK-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000007664 blowing Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 3
IXZMRVOOBBPFIZ-UHFFFAOYSA-N 4-nitro-3h-1,3-benzoxazol-2-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1NC(=O)O2 IXZMRVOOBBPFIZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
239000002994 raw material Substances 0.000 description 3
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 1
ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
AGSLHFQPWVSWHT-UHFFFAOYSA-N 5,7-dibromo-3h-1,3-benzoxazol-2-one Chemical compound BrC1=CC(Br)=C2OC(=O)NC2=C1 AGSLHFQPWVSWHT-UHFFFAOYSA-N 0.000 description 1
UXRRICZTIWOWDF-UHFFFAOYSA-N 5-chloro-6-nitro-3h-1,3-benzoxazol-2-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1NC(=O)O2 UXRRICZTIWOWDF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
TZFWDZFKRBELIQ-UHFFFAOYSA-N chlorzoxazone Chemical compound ClC1=CC=C2OC(O)=NC2=C1 TZFWDZFKRBELIQ-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000007599 discharging Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

JP2663079A 1979-03-09 1979-03-09 Production of benzoxazolone compound Granted JPS55120572A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP2663079A JPS55120572A (en)	1979-03-09	1979-03-09	Production of benzoxazolone compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2663079A JPS55120572A (en)	1979-03-09	1979-03-09	Production of benzoxazolone compound

Publications (2)

Publication Number	Publication Date
JPS55120572A JPS55120572A (en)	1980-09-17
JPS6160833B2 true JPS6160833B2 (de)	1986-12-23

Family

ID=12198762

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2663079A Granted JPS55120572A (en)	1979-03-09	1979-03-09	Production of benzoxazolone compound

Country Status (1)

Country	Link
JP (1)	JPS55120572A (de)

1979
- 1979-03-09 JP JP2663079A patent/JPS55120572A/ja active Granted

Also Published As

Publication number	Publication date
JPS55120572A (en)	1980-09-17

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