CN103333130B - 4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5(4h)-酮的制备方法 - Google Patents
4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5(4h)-酮的制备方法 Download PDFInfo
- Publication number
- CN103333130B CN103333130B CN201310275483.1A CN201310275483A CN103333130B CN 103333130 B CN103333130 B CN 103333130B CN 201310275483 A CN201310275483 A CN 201310275483A CN 103333130 B CN103333130 B CN 103333130B
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- Prior art keywords
- triazine
- amino
- tertiary butyl
- acetone
- methylthio group
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 64
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 17
- 238000009413 insulation Methods 0.000 claims abstract description 17
- 229960004839 potassium iodide Drugs 0.000 claims abstract description 17
- 235000007715 potassium iodide Nutrition 0.000 claims abstract description 17
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 3
- 238000004457 water analysis Methods 0.000 claims abstract description 3
- OFKAVNQBCRJBJE-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC(C)(C)C1=NNC(=S)N(N)C1=O OFKAVNQBCRJBJE-UHFFFAOYSA-N 0.000 claims description 17
- 238000013019 agitation Methods 0.000 claims description 9
- 238000001291 vacuum drying Methods 0.000 claims description 9
- JJUMRPCLXYQXJO-UHFFFAOYSA-N 4-butyl-3-sulfanylidene-2H-1,2,4-triazin-5-one Chemical group C(CCC)N1C(=NN=CC1=O)S JJUMRPCLXYQXJO-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000010812 external standard method Methods 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WCYAALZQFZMMOM-UHFFFAOYSA-N methanol;sulfuric acid Chemical compound OC.OS(O)(=O)=O WCYAALZQFZMMOM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- 241000230452 Cyclothone braueri Species 0.000 description 1
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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CN201310275483.1A CN103333130B (zh) | 2013-07-03 | 2013-07-03 | 4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5(4h)-酮的制备方法 |
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CN201310275483.1A CN103333130B (zh) | 2013-07-03 | 2013-07-03 | 4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5(4h)-酮的制备方法 |
Publications (2)
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CN103333130A CN103333130A (zh) | 2013-10-02 |
CN103333130B true CN103333130B (zh) | 2016-04-06 |
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CN201310275483.1A Active CN103333130B (zh) | 2013-07-03 | 2013-07-03 | 4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5(4h)-酮的制备方法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109320470A (zh) * | 2018-10-31 | 2019-02-12 | 江苏七洲绿色化工股份有限公司 | 一种嗪草酮的制备方法及废液的处理方法 |
Families Citing this family (1)
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CN110606832B (zh) * | 2019-09-30 | 2021-11-26 | 江苏七洲绿色化工股份有限公司 | 一种嗪草酮的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030216573A1 (en) * | 2002-05-16 | 2003-11-20 | Jackman Dennis E. | Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones |
CN101899016A (zh) * | 2009-05-27 | 2010-12-01 | 北京紫光英力化工技术有限公司 | 嗪草酮甲基化母液回收利用新工艺 |
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2013
- 2013-07-03 CN CN201310275483.1A patent/CN103333130B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030216573A1 (en) * | 2002-05-16 | 2003-11-20 | Jackman Dennis E. | Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones |
CN101899016A (zh) * | 2009-05-27 | 2010-12-01 | 北京紫光英力化工技术有限公司 | 嗪草酮甲基化母液回收利用新工艺 |
Non-Patent Citations (3)
Title |
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4-氨基-2-甲氧基-5-乙硫基苯甲酸的合成;朱占元等;《淮阴工学院学报》;20100215;第19卷(第1期);第70页左栏1.2.4部分 * |
Alkylation of 4-amino-3-mercapto-1,2,4-triazin-5(4H)-ones and oxidation of the products;Fritz Sauter等;《Journal of Chemical Research (Synopses)》;19861231(第9期);第320页流程1和表1 * |
Regioselectivity in the amination of methylsulfanyl-substituted azines with O-mesitylenesulfonylhydroxylamine;G.I.Borodkin等;《Russian Journal of Organic Chemistry》;20100630;第46卷(第6期);第915页左栏倒数第2段 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109320470A (zh) * | 2018-10-31 | 2019-02-12 | 江苏七洲绿色化工股份有限公司 | 一种嗪草酮的制备方法及废液的处理方法 |
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Address after: 226400 No. two, No. 18, Haibin Road, Rudong Coastal Economic Development Zone, Nantong, Jiangsu Patentee after: Jiangsu Ruibang agrochemical Co.,Ltd. Address before: 226407, Jiangsu, Nantong province Rudong County mouth chemical gathering area Patentee before: JIANGSU REPONT PESTICIDE FACTORY Co.,Ltd. |
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Address after: No. 18 Haiyou Road, Yangkou Town, Rudong County, Nantong City, Jiangsu Province, 226400 Patentee after: Jiangsu Ruibang agrochemical Co.,Ltd. Country or region after: China Address before: 226400 18 Haibin 2nd Road, Rudong Coastal Economic Development Zone, Nantong City, Jiangsu Province Patentee before: Jiangsu Ruibang agrochemical Co.,Ltd. Country or region before: China |
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