CN101863840B - Preparation method of 5-amino-6-methyl benzimidazolone - Google Patents
Preparation method of 5-amino-6-methyl benzimidazolone Download PDFInfo
- Publication number
- CN101863840B CN101863840B CN2010102020482A CN201010202048A CN101863840B CN 101863840 B CN101863840 B CN 101863840B CN 2010102020482 A CN2010102020482 A CN 2010102020482A CN 201010202048 A CN201010202048 A CN 201010202048A CN 101863840 B CN101863840 B CN 101863840B
- Authority
- CN
- China
- Prior art keywords
- preparation
- methyl
- methyl benzimidazolone
- amino
- benzimidazolone
- 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 - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 5-amino-6-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C(N)C(C)=CC2=C1NC(=O)N2 ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000006722 reduction reaction Methods 0.000 claims abstract description 23
- IOQXONVXJBPYAB-UHFFFAOYSA-N 5-methyl-6-nitrobenzimidazol-2-one Chemical compound C1=C([N+]([O-])=O)C(C)=CC2=NC(=O)N=C21 IOQXONVXJBPYAB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- CTCHXZUMFHNSHM-UHFFFAOYSA-N 5-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound CC1=CC=C2NC(=O)NC2=C1 CTCHXZUMFHNSHM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004202 carbamide Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 238000006396 nitration reaction Methods 0.000 claims abstract description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- MEVPRMYSNBGYJU-UHFFFAOYSA-N 5-amino-6-methylbenzimidazol-2-one Chemical class C1=C(N)C(C)=CC2=NC(=O)N=C21 MEVPRMYSNBGYJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 238000011946 reduction process Methods 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- 238000009413 insulation Methods 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 238000013019 agitation Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000004062 sedimentation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 241001411320 Eriogonum inflatum Species 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000010009 beating Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001546 nitrifying effect Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010102020482A CN101863840B (en) | 2010-06-18 | 2010-06-18 | Preparation method of 5-amino-6-methyl benzimidazolone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010102020482A CN101863840B (en) | 2010-06-18 | 2010-06-18 | Preparation method of 5-amino-6-methyl benzimidazolone |
Publications (2)
Publication Number | Publication Date |
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CN101863840A CN101863840A (en) | 2010-10-20 |
CN101863840B true CN101863840B (en) | 2011-11-16 |
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CN2010102020482A Expired - Fee Related CN101863840B (en) | 2010-06-18 | 2010-06-18 | Preparation method of 5-amino-6-methyl benzimidazolone |
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CN (1) | CN101863840B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102295605B (en) * | 2011-06-22 | 2014-07-23 | 华东理工大学 | Method for preparing benzimidazolone derivative |
CN107365273B (en) * | 2017-08-11 | 2020-01-24 | 东营市天正化工有限公司 | Production method for synthesizing 5-nitrobenzimidazole ketone by one-pot method |
CN109627219A (en) * | 2018-12-29 | 2019-04-16 | 高邮市华宝颜料有限公司 | A kind of production method of 5- amino-6-methyl benzimidazolone |
CN110256435A (en) * | 2019-07-04 | 2019-09-20 | 绍兴市精益生物化工有限公司 | One-step synthesis method of 1, 3-dimethyl uric acid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6087480A (en) * | 1998-01-13 | 2000-07-11 | Ciba Specialty Chemcals Corporation | Process for preparing sparingly soluble aromatic amines |
CN1675185A (en) * | 2002-06-07 | 2005-09-28 | 科蒂科股份有限公司 | Therapeutic molecules and methods-1 |
-
2010
- 2010-06-18 CN CN2010102020482A patent/CN101863840B/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6087480A (en) * | 1998-01-13 | 2000-07-11 | Ciba Specialty Chemcals Corporation | Process for preparing sparingly soluble aromatic amines |
CN1675185A (en) * | 2002-06-07 | 2005-09-28 | 科蒂科股份有限公司 | Therapeutic molecules and methods-1 |
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CN101863840A (en) | 2010-10-20 |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20101020 Assignee: GAOYOU HUABAO PIGMENT Co.,Ltd. Assignor: Zibo Shengma Chemical Plant Contract record no.: 2013320000739 Denomination of invention: Preparation method of 5-amino-6-methyl benzimidazolone Granted publication date: 20111116 License type: Exclusive License Record date: 20131105 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
CP01 | Change in the name or title of a patent holder |
Address after: 255095, Zhangdian District, Shandong City, Zibo province Zhen Zhen Ma camp village north Patentee after: ZIBO SHENGMA CHEMICAL Co.,Ltd. Address before: 255095, Zhangdian District, Shandong City, Zibo province Zhen Zhen Ma camp village north Patentee before: Zibo Shengma Chemical Plant |
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CP01 | Change in the name or title of a patent holder | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20111116 |
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CF01 | Termination of patent right due to non-payment of annual fee |