CN1594287A - 3-羟基丙烯腈金属盐的制备方法 - Google Patents
3-羟基丙烯腈金属盐的制备方法 Download PDFInfo
- Publication number
- CN1594287A CN1594287A CN 200410052900 CN200410052900A CN1594287A CN 1594287 A CN1594287 A CN 1594287A CN 200410052900 CN200410052900 CN 200410052900 CN 200410052900 A CN200410052900 A CN 200410052900A CN 1594287 A CN1594287 A CN 1594287A
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- CN
- China
- Prior art keywords
- hydroxyacrylonitrile
- acetonitrile
- metal salt
- formate
- sodium
- 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.)
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- VLQQXSKNYWXJKT-HNQUOIGGSA-N (e)-3-hydroxyprop-2-enenitrile Chemical compound O\C=C\C#N VLQQXSKNYWXJKT-HNQUOIGGSA-N 0.000 title claims abstract description 72
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 31
- 239000002184 metal Substances 0.000 title claims abstract description 31
- 150000003839 salts Chemical class 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 204
- 238000006482 condensation reaction Methods 0.000 claims abstract description 10
- -1 formic acid ester Chemical class 0.000 claims abstract description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract 4
- 235000019253 formic acid Nutrition 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- 239000012266 salt solution Substances 0.000 claims description 50
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 36
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical group COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 30
- 159000000000 sodium salts Chemical class 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical group [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910001414 potassium ion Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 abstract description 40
- 229940104302 cytosine Drugs 0.000 abstract description 20
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 19
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010606 normalization Methods 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GAKUKXZINODJOH-UHFFFAOYSA-N cyclobutyl formate Chemical compound O=COC1CCC1 GAKUKXZINODJOH-UHFFFAOYSA-N 0.000 description 2
- XKFJCDJMZOJCNL-UHFFFAOYSA-N cyclobutylmethyl formate Chemical compound O=COCC1CCC1 XKFJCDJMZOJCNL-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VLQQXSKNYWXJKT-UHFFFAOYSA-N 3-hydroxyprop-2-enenitrile Chemical compound OC=CC#N VLQQXSKNYWXJKT-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 229950011487 enocitabine Drugs 0.000 description 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
实施例名称 | 质量(g) | 熔点(℃) | 含量(HPLC,面积归一法) | 含量(HPLC,对照品法) | 收率(以乙腈计) |
实施例5 | 134 | >280 | 99.0% | 99.8% | 55.1% |
实施例6 | 133 | >280 | 99.2% | 99.8% | 54.7% |
实施例7 | 133 | >280 | 99.0% | 99.9% | 54.7% |
实施例7 | 132 | >280 | 99.1% | 99.8% | 54.3% |
实施例8 | 132 | >280 | 99.2% | 99.9% | 54.3% |
实施例9 | 131 | >280 | 99.1% | 99.9% | 53.9% |
实施例10 | 133 | >280 | 99.0% | 99.8% | 54.7% |
实施例11 | 130 | >280 | 99.1% | 99.9% | 53.5% |
实施例12 | 131 | >280 | 99.2% | 99.9% | 53.9% |
实施例13 | 132 | >280 | 99.1% | 99.8% | 54.3% |
实施例14 | 134 | >280 | 99.0% | 99.9% | 55.1% |
实施例15 | 135 | >280 | 99.1% | 99.8% | 53.5% |
实施例16 | 132 | >280 | 99.0% | 99.8% | 54.3% |
实施例17 | 136 | >280 | 99.0% | 99.9% | 56.0% |
实施例18 | 134 | >280 | 99.0% | 99.8% | 55.1% |
实施例19 | 133 | >280 | 99.2% | 99.8% | 54.7% |
实施例20 | 133 | >280 | 99.0% | 99.9% | 54.7% |
实施例21 | 132 | >280 | 99.1% | 99.8% | 54.3% |
实施例22 | 132 | >280 | 99.2% | 99.9% | 54.3% |
实施例23 | 131 | >280 | 99.1% | 99.9% | 53.9% |
实施例24 | 133 | >280 | 99.0% | 99.8% | 54.7% |
实施例25 | 130 | >280 | 99.1% | 99.9% | 53.5% |
实施例26 | 131 | >280 | 99.2% | 99.9% | 53.9% |
实施例27 | 132 | >280 | 99.1% | 99.8% | 54.3% |
实施例28 | 134 | >280 | 99.0% | 99.9% | 55.1% |
实施例29 | 135 | >280 | 99.1% | 99.8% | 53.5% |
实施例30 | 132 | >280 | 99.0% | 99.8% | 54.3% |
实施例31 | 136 | >280 | 99.0% | 99.9% | 56.0% |
实施例32 | 134 | >280 | 99.0% | 99.8% | 55.1% |
实施例33 | 133 | >280 | 99.2% | 99.8% | 54.7% |
实施例34 | 133 | >280 | 99.0% | 99.9% | 54.7% |
实施例35 | 132 | >280 | 99.1% | 99.8% | 54.3% |
实施例36 | 132 | >280 | 99.2% | 99.9% | 54.3% |
实施例37 | 131 | >280 | 99.1% | 99.9% | 53.9% |
实施例38 | 133 | >280 | 99.0% | 99.8% | 54.7% |
实施例39 | 130 | >280 | 99.1% | 99.9% | 53.5% |
实施例40 | 131 | >280 | 99.2% | 99.9% | 53.9% |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 200410052900 CN1226282C (zh) | 2004-07-16 | 2004-07-16 | 3-羟基丙烯腈金属盐的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN 200410052900 CN1226282C (zh) | 2004-07-16 | 2004-07-16 | 3-羟基丙烯腈金属盐的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN1594287A true CN1594287A (zh) | 2005-03-16 |
CN1226282C CN1226282C (zh) | 2005-11-09 |
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Application Number | Title | Priority Date | Filing Date |
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CN 200410052900 Expired - Lifetime CN1226282C (zh) | 2004-07-16 | 2004-07-16 | 3-羟基丙烯腈金属盐的制备方法 |
Country Status (1)
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CN (1) | CN1226282C (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880758A (zh) * | 2014-03-24 | 2014-06-25 | 浙江先锋科技有限公司 | 胞嘧啶的合成方法 |
CN103896858A (zh) * | 2014-03-24 | 2014-07-02 | 浙江先锋科技有限公司 | 胞嘧啶的制备工艺 |
CN103896859A (zh) * | 2014-03-24 | 2014-07-02 | 浙江先锋科技有限公司 | 合成胞嘧啶的工艺 |
CN104086489A (zh) * | 2013-04-01 | 2014-10-08 | 北京澳林森科技有限公司 | 一种合成5-氟胞嘧啶的新工艺 |
CN106588921A (zh) * | 2017-01-13 | 2017-04-26 | 菏泽学院 | 一种7‑氮杂吲哚‑3‑甲酸甲酯的合成方法 |
CN106749041A (zh) * | 2016-12-29 | 2017-05-31 | 新乡制药股份有限公司 | 一种合成胞嘧啶的方法 |
CN109912454A (zh) * | 2019-03-26 | 2019-06-21 | 南京欧信医药技术有限公司 | 3-乙氧基丙烯腈和3,3-二乙氧基丙腈混合物的合成方法 |
CN115611815A (zh) * | 2022-10-10 | 2023-01-17 | 新乡瑞诺药业有限公司 | 一种胞嘧啶合成方法 |
-
2004
- 2004-07-16 CN CN 200410052900 patent/CN1226282C/zh not_active Expired - Lifetime
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104086489A (zh) * | 2013-04-01 | 2014-10-08 | 北京澳林森科技有限公司 | 一种合成5-氟胞嘧啶的新工艺 |
CN103896858B (zh) * | 2014-03-24 | 2016-08-17 | 浙江先锋科技股份有限公司 | 胞嘧啶的制备工艺 |
CN103896859A (zh) * | 2014-03-24 | 2014-07-02 | 浙江先锋科技有限公司 | 合成胞嘧啶的工艺 |
CN103896858A (zh) * | 2014-03-24 | 2014-07-02 | 浙江先锋科技有限公司 | 胞嘧啶的制备工艺 |
CN103896859B (zh) * | 2014-03-24 | 2016-08-17 | 浙江先锋科技股份有限公司 | 合成胞嘧啶的工艺 |
CN103880758B (zh) * | 2014-03-24 | 2016-08-17 | 浙江先锋科技股份有限公司 | 胞嘧啶的合成方法 |
CN103880758A (zh) * | 2014-03-24 | 2014-06-25 | 浙江先锋科技有限公司 | 胞嘧啶的合成方法 |
CN106749041A (zh) * | 2016-12-29 | 2017-05-31 | 新乡制药股份有限公司 | 一种合成胞嘧啶的方法 |
CN106588921A (zh) * | 2017-01-13 | 2017-04-26 | 菏泽学院 | 一种7‑氮杂吲哚‑3‑甲酸甲酯的合成方法 |
CN106588921B (zh) * | 2017-01-13 | 2018-02-13 | 菏泽学院 | 一种7‑氮杂吲哚‑3‑甲酸甲酯的合成方法 |
CN109912454A (zh) * | 2019-03-26 | 2019-06-21 | 南京欧信医药技术有限公司 | 3-乙氧基丙烯腈和3,3-二乙氧基丙腈混合物的合成方法 |
CN109912454B (zh) * | 2019-03-26 | 2022-01-21 | 南京欧信医药技术有限公司 | 3-乙氧基丙烯腈和3,3-二乙氧基丙腈混合物的合成方法 |
CN115611815A (zh) * | 2022-10-10 | 2023-01-17 | 新乡瑞诺药业有限公司 | 一种胞嘧啶合成方法 |
Also Published As
Publication number | Publication date |
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