JP5268264B2 - アルカンジスルホニルハライドの製造方法 - Google Patents
アルカンジスルホニルハライドの製造方法 Download PDFInfo
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- JP5268264B2 JP5268264B2 JP2007027445A JP2007027445A JP5268264B2 JP 5268264 B2 JP5268264 B2 JP 5268264B2 JP 2007027445 A JP2007027445 A JP 2007027445A JP 2007027445 A JP2007027445 A JP 2007027445A JP 5268264 B2 JP5268264 B2 JP 5268264B2
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- JP
- Japan
- Prior art keywords
- halide
- formula
- phosphoryl
- phosphorus
- alkanedisulfonyl
- 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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- 150000004820 halides Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- -1 phosphorus halide Chemical class 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 239000011574 phosphorus Substances 0.000 claims abstract description 10
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 3
- DKZQZHQHDMVGHE-UHFFFAOYSA-N methanedisulfonyl chloride Chemical compound ClS(=O)(=O)CS(Cl)(=O)=O DKZQZHQHDMVGHE-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
撹拌機、冷却管および温度計を備え付けた500ml容の四つ口フラスコにメタンジスルホン酸140.9g(0.8モル)および塩化ホスホリル150ml(246.8g)を仕込み、撹拌下、50℃で五塩化りん366.5g(1.76モル)を4時間かけて添加した。添加終了後、反応液を50℃に維持して30分間撹拌した。その後、115℃まで昇温して減圧下で未反応の塩化ホスホリルを留去し、引き続き同温度にてさらに減圧蒸留することにより、前記式(2)におけるR1およびR2が共に水素原子であり、nが1であり、Xが塩素原子である、微黄色透明オイル状のメタンジスルホニルクロリド160.7gを得た。得られたメタンジスルホニルクロリドの収率は、メタンジスルホン酸に対して94.3モル%であった。
沸点:180℃/2Torr
1H−NMR(400MHz、CDCl3)δ(ppm):5.56(s,2H)
Claims (3)
- 式(1):
前記ハロゲン化りん(V)のハロゲン原子と、前記ハロゲン化ホスホリルのハロゲン原子とが、同一種である、
式(2):
- ハロゲン化ホスホリルが塩化ホスホリルである、請求項1に記載のアルカンジスルホニルハライドの製造方法。
- ハロゲン化りん(V)が五塩化りんであり、式(2)におけるXが塩素原子である、請求項1又は2に記載のアルカンジスルホニルハライドの製造方法。
Priority Applications (1)
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JP2007027445A JP5268264B2 (ja) | 2007-02-07 | 2007-02-07 | アルカンジスルホニルハライドの製造方法 |
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JP2007027445A JP5268264B2 (ja) | 2007-02-07 | 2007-02-07 | アルカンジスルホニルハライドの製造方法 |
Publications (2)
Publication Number | Publication Date |
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JP2008189612A JP2008189612A (ja) | 2008-08-21 |
JP5268264B2 true JP5268264B2 (ja) | 2013-08-21 |
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Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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JP3444477B2 (ja) * | 1998-12-28 | 2003-09-08 | セントラル硝子株式会社 | トリフルオロメタンスルホニルクロリドの製造方法 |
JP3963607B2 (ja) * | 1999-03-16 | 2007-08-22 | セントラル硝子株式会社 | トリフルオロメタンスルホニルクロリドの製造方法 |
AU1413301A (en) * | 1999-11-17 | 2001-05-30 | Sumitomo Pharmaceuticals Company, Limited | Diabetic remedy containing dipiperazine derivative |
GB0029356D0 (en) * | 2000-12-01 | 2001-01-17 | Avecia Ltd | Transfer hydrogenation |
DE10210590A1 (de) * | 2002-03-11 | 2003-10-02 | Curacyte Ag | Hemmstoffe des Gerinnungsfaktors Xa, ihre Herstellung und Verwendung |
DE60306636T2 (de) * | 2002-04-09 | 2007-07-05 | Eli Lilly And Co., Indianapolis | Wachstumhormonsekretionsförderer |
GB0228552D0 (en) * | 2002-12-06 | 2003-01-15 | Glaxo Group Ltd | Chemical compounds |
JP4577482B2 (ja) * | 2004-02-06 | 2010-11-10 | 日本電気株式会社 | リチウム二次電池用電解液およびそれを用いたリチウム二次電池 |
JP4577499B2 (ja) * | 2005-01-28 | 2010-11-10 | 日本電気株式会社 | メチレンジスルホニルクロライド及びその誘導体の製造方法 |
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