JPWO2019208807A5 - - Google Patents
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- JPWO2019208807A5 JPWO2019208807A5 JP2020515623A JP2020515623A JPWO2019208807A5 JP WO2019208807 A5 JPWO2019208807 A5 JP WO2019208807A5 JP 2020515623 A JP2020515623 A JP 2020515623A JP 2020515623 A JP2020515623 A JP 2020515623A JP WO2019208807 A5 JPWO2019208807 A5 JP WO2019208807A5
- Authority
- JP
- Japan
- Prior art keywords
- compound represented
- formula
- mol
- carboxylic acid
- halogenating agent
- 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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- -1 nitrile compound Chemical class 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 230000002140 halogenating effect Effects 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 4
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 230000002862 amidating effect Effects 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims 14
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims 14
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 239000002994 raw material Substances 0.000 claims 6
- 150000003457 sulfones Chemical group 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 150000002430 hydrocarbons Chemical class 0.000 claims 4
- 238000006386 neutralization reaction Methods 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 239000002808 molecular sieve Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 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 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Images
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862663014P | 2018-04-26 | 2018-04-26 | |
| US62/663,014 | 2018-04-26 | ||
| US201862780445P | 2018-12-17 | 2018-12-17 | |
| US62/780,445 | 2018-12-17 | ||
| PCT/JP2019/018065 WO2019208807A1 (ja) | 2018-04-26 | 2019-04-26 | 芳香族ニトリル化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2019208807A1 JPWO2019208807A1 (ja) | 2021-04-30 |
| JPWO2019208807A5 true JPWO2019208807A5 (https=) | 2022-05-09 |
| JP7399850B2 JP7399850B2 (ja) | 2023-12-18 |
Family
ID=68294176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020515623A Active JP7399850B2 (ja) | 2018-04-26 | 2019-04-26 | 芳香族ニトリル化合物の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US12054448B2 (https=) |
| EP (2) | EP3786152B1 (https=) |
| JP (1) | JP7399850B2 (https=) |
| KR (2) | KR102796989B1 (https=) |
| CN (3) | CN118439973A (https=) |
| CA (1) | CA3098437C (https=) |
| ES (1) | ES3015171T3 (https=) |
| PL (1) | PL3786152T3 (https=) |
| WO (1) | WO2019208807A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018159028A1 (ja) * | 2017-03-01 | 2018-09-07 | 株式会社エーピーアイ コーポレーション | Ｎ－ベンジル－２－ブロモ－３－メトキシプロピオン酸アミド及びその中間体の製造方法 |
| WO2021085468A1 (ja) * | 2019-10-29 | 2021-05-06 | 株式会社エーピーアイ コーポレーション | 高純度２－ナフチルアセトニトリル及びその製造方法 |
| CN115784929B (zh) * | 2022-12-21 | 2023-10-13 | 浦拉司科技（上海）有限责任公司 | 一种巴豆腈的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268650A (ja) * | 1985-05-21 | 1986-11-28 | Otsuka Pharmaceut Factory Inc | ナフトキノン誘導体 |
| JP2001039904A (ja) | 1999-07-29 | 2001-02-13 | Sumikin Chemical Co Ltd | ブロモアルキルナフタレンの製造方法 |
| SE0201938D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New process |
| NZ592836A (en) | 2005-07-27 | 2013-01-25 | Dov Pharmaceutical Inc | Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders |
| JP2010268650A (ja) * | 2009-05-18 | 2010-11-25 | Daikin Ind Ltd | アキシャルギャップ型回転電機 |
| WO2014001939A1 (en) | 2012-06-30 | 2014-01-03 | Alembic Pharmaceuticals Limited | Process for preparation of agomelatine and crystalline form i thereof |
| KR20160101012A (ko) | 2013-12-09 | 2016-08-24 | 뉴로반스, 인크. | 신규 조성물 |
| WO2021085468A1 (ja) | 2019-10-29 | 2021-05-06 | 株式会社エーピーアイ コーポレーション | 高純度２－ナフチルアセトニトリル及びその製造方法 |
-
2019
- 2019-04-26 JP JP2020515623A patent/JP7399850B2/ja active Active
- 2019-04-26 PL PL19793649.5T patent/PL3786152T3/pl unknown
- 2019-04-26 KR KR1020207033680A patent/KR102796989B1/ko active Active
- 2019-04-26 US US17/050,255 patent/US12054448B2/en active Active
- 2019-04-26 WO PCT/JP2019/018065 patent/WO2019208807A1/ja not_active Ceased
- 2019-04-26 CA CA3098437A patent/CA3098437C/en active Active
- 2019-04-26 EP EP19793649.5A patent/EP3786152B1/en active Active
- 2019-04-26 CN CN202410519014.8A patent/CN118439973A/zh active Pending
- 2019-04-26 CN CN201980028082.1A patent/CN112041298A/zh active Pending
- 2019-04-26 CN CN202510449366.5A patent/CN120441453A/zh active Pending
- 2019-04-26 KR KR1020247025451A patent/KR20240121346A/ko active Pending
- 2019-04-26 ES ES19793649T patent/ES3015171T3/es active Active
- 2019-04-26 EP EP24219154.2A patent/EP4520753A3/en active Pending
-
2024
- 2024-06-10 US US18/738,245 patent/US20240351978A1/en active Pending
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