CN1164564C - Process for preparing high purity 2-amino-5-chloro-2'-diphenyl ketone - Google Patents
Process for preparing high purity 2-amino-5-chloro-2'-diphenyl ketone Download PDFInfo
- Publication number
- CN1164564C CN1164564C CNB011184752A CN01118475A CN1164564C CN 1164564 C CN1164564 C CN 1164564C CN B011184752 A CNB011184752 A CN B011184752A CN 01118475 A CN01118475 A CN 01118475A CN 1164564 C CN1164564 C CN 1164564C
- Authority
- CN
- China
- Prior art keywords
- fluoro
- chloro
- amino
- preparation
- fab
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 36
- 239000011592 zinc chloride Substances 0.000 claims abstract description 18
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000018044 dehydration Effects 0.000 claims abstract description 6
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 10
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 claims description 8
- DWFDQVMFSLLMPE-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1 DWFDQVMFSLLMPE-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
- 239000012965 benzophenone Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XYGVIBXOJOOCFR-BTJKTKAUSA-N (z)-but-2-enedioic acid;8-chloro-6-(2-fluorophenyl)-1-methyl-4h-imidazo[1,5-a][1,4]benzodiazepine Chemical compound OC(=O)\C=C/C(O)=O.C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F XYGVIBXOJOOCFR-BTJKTKAUSA-N 0.000 description 1
- ZIIJJOPLRSCQNX-UHFFFAOYSA-N Flurazepam hydrochloride Chemical compound Cl.Cl.N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ZIIJJOPLRSCQNX-UHFFFAOYSA-N 0.000 description 1
- WMFSSTNVXWNLKI-UHFFFAOYSA-N Flutazolam Chemical compound O1CCN2CC(=O)N(CCO)C3=CC=C(Cl)C=C3C21C1=CC=CC=C1F WMFSSTNVXWNLKI-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229950009354 flutazolam Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Project | Prior art | The present invention |
Fusing point | 88-92℃ | 94-97℃ |
HPLC content | ≤95% | ≥98% |
Total recovery | 50% | 70% |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB011184752A CN1164564C (en) | 2001-06-01 | 2001-06-01 | Process for preparing high purity 2-amino-5-chloro-2'-diphenyl ketone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB011184752A CN1164564C (en) | 2001-06-01 | 2001-06-01 | Process for preparing high purity 2-amino-5-chloro-2'-diphenyl ketone |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1326924A CN1326924A (en) | 2001-12-19 |
CN1164564C true CN1164564C (en) | 2004-09-01 |
Family
ID=4663215
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB011184752A Expired - Fee Related CN1164564C (en) | 2001-06-01 | 2001-06-01 | Process for preparing high purity 2-amino-5-chloro-2'-diphenyl ketone |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1164564C (en) |
-
2001
- 2001-06-01 CN CNB011184752A patent/CN1164564C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN1326924A (en) | 2001-12-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
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 | ||
ASS | Succession or assignment of patent right |
Owner name: NINGBO RENJIAN MEDICAL CHEMICAL CO., LTD. Free format text: FORMER OWNER: CEN JIAN Effective date: 20100527 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 315300 NO.398, N.2ND RING MIDDLE ROAD, CIXI CITY, ZHEJIANG PROVINCE TO: 315204 NO.255, BEIHAI ROAD, NINGBO CHEMICAL ENGINEERING DISTRICT, ZHEJIANG PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20100527 Address after: 315204 No. 255 North Sea Road, Ningbo chemical industry zone, Zhejiang Patentee after: Ningbo Renjian Pharmaceutical Co., Ltd. Address before: 315300 No. 398 North Second Ring Road, Zhejiang, Cixi Patentee before: Cen Jian |
|
C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20040901 Termination date: 20130601 |