CS240955B2 - Production method of in core substituted benzylhalogenides - Google Patents
Production method of in core substituted benzylhalogenides Download PDFInfo
- Publication number
- CS240955B2 CS240955B2 CS831829A CS182983A CS240955B2 CS 240955 B2 CS240955 B2 CS 240955B2 CS 831829 A CS831829 A CS 831829A CS 182983 A CS182983 A CS 182983A CS 240955 B2 CS240955 B2 CS 240955B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- chloromethyl
- substituted
- halide
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 33
- -1 benzylic halides Chemical class 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- HTMQZWFSTJVJEQ-UHFFFAOYSA-N benzylsulfinylmethylbenzene Chemical class C=1C=CC=CC=1CS(=O)CC1=CC=CC=C1 HTMQZWFSTJVJEQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 24
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 150000004820 halides Chemical class 0.000 abstract description 16
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 238000006956 Pummerer reaction Methods 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 230000005587 bubbling Effects 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
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- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 5
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- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- REIWBMTUTDSMAI-UHFFFAOYSA-N 2-(chloromethyl)-6-(trifluoromethyl)aniline;hydrochloride Chemical compound [Cl-].[NH3+]C1=C(CCl)C=CC=C1C(F)(F)F REIWBMTUTDSMAI-UHFFFAOYSA-N 0.000 description 3
- VTZUPSQTUXHGHB-UHFFFAOYSA-N 2-[(2-aminophenyl)methylsulfinylmethyl]aniline Chemical compound NC1=CC=CC=C1CS(=O)CC1=CC=CC=C1N VTZUPSQTUXHGHB-UHFFFAOYSA-N 0.000 description 3
- AKZWHYLRQANKGA-UHFFFAOYSA-N 2-amino-3-(chloromethyl)benzonitrile Chemical compound NC1=C(CCl)C=CC=C1C#N AKZWHYLRQANKGA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- CTLRITSBJZQTNM-UHFFFAOYSA-N 2-(chloromethyl)-6-(trifluoromethyl)aniline Chemical compound NC1=C(CCl)C=CC=C1C(F)(F)F CTLRITSBJZQTNM-UHFFFAOYSA-N 0.000 description 2
- JFJQMUQRTCGSFC-UHFFFAOYSA-N 2-(chloromethyl)aniline Chemical class NC1=CC=CC=C1CCl JFJQMUQRTCGSFC-UHFFFAOYSA-N 0.000 description 2
- AWUFEMPPABUXSZ-UHFFFAOYSA-N 2-(methylsulfanylmethyl)-6-(trifluoromethyl)aniline Chemical compound CSCC1=CC=CC(C(F)(F)F)=C1N AWUFEMPPABUXSZ-UHFFFAOYSA-N 0.000 description 2
- QTEYDTXRTCNUCO-UHFFFAOYSA-N 2-(methylsulfinylmethyl)-6-(trifluoromethyl)aniline Chemical compound CS(=O)CC1=CC=CC(C(F)(F)F)=C1N QTEYDTXRTCNUCO-UHFFFAOYSA-N 0.000 description 2
- UKFBSHNQPVYKIX-UHFFFAOYSA-N 7$l^{4}-thiabicyclo[4.1.0]hepta-1,3,5-triene 7-oxide Chemical compound C1=CC=C2S(=O)C2=C1 UKFBSHNQPVYKIX-UHFFFAOYSA-N 0.000 description 2
- OFQPKKGMNWASPN-UHFFFAOYSA-N Benzyl methyl sulfide Chemical compound CSCC1=CC=CC=C1 OFQPKKGMNWASPN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LISVNGUOWUKZQY-UHFFFAOYSA-N Methyl benzyl sulfoxide Chemical compound CS(=O)CC1=CC=CC=C1 LISVNGUOWUKZQY-UHFFFAOYSA-N 0.000 description 2
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- 238000010533 azeotropic distillation Methods 0.000 description 2
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- RFIZPYFNEYSHKG-UHFFFAOYSA-N pyrrolidine-2,5-dione;sodium Chemical compound [Na].O=C1CCC(=O)N1 RFIZPYFNEYSHKG-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35896682A | 1982-03-17 | 1982-03-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS182983A2 CS182983A2 (en) | 1985-06-13 |
| CS240955B2 true CS240955B2 (en) | 1986-03-13 |
Family
ID=23411756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS831829A CS240955B2 (en) | 1982-03-17 | 1983-03-16 | Production method of in core substituted benzylhalogenides |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0089330B1 (de) |
| JP (1) | JPS58167525A (de) |
| KR (1) | KR870000246B1 (de) |
| AT (1) | ATE26698T1 (de) |
| AU (1) | AU562361B2 (de) |
| CS (1) | CS240955B2 (de) |
| DD (1) | DD207903A5 (de) |
| DE (1) | DE3371068D1 (de) |
| GB (1) | GB2117380B (de) |
| HU (1) | HU189673B (de) |
| MY (1) | MY8700115A (de) |
| NZ (1) | NZ203592A (de) |
| PL (1) | PL241049A1 (de) |
| PT (1) | PT76398B (de) |
| RO (1) | RO87596B (de) |
| ZA (1) | ZA831840B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4779311B2 (ja) * | 2004-06-21 | 2011-09-28 | 井関農機株式会社 | ひまわり収穫機 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3894034A (en) * | 1973-01-29 | 1975-07-08 | Ohio State Res Found | A process for producing azasulfonium salts |
-
1983
- 1983-03-15 DE DE8383870021T patent/DE3371068D1/de not_active Expired
- 1983-03-15 AT AT83870021T patent/ATE26698T1/de active
- 1983-03-15 EP EP83870021A patent/EP0089330B1/de not_active Expired
- 1983-03-16 HU HU83893A patent/HU189673B/hu unknown
- 1983-03-16 AU AU12492/83A patent/AU562361B2/en not_active Ceased
- 1983-03-16 KR KR1019830001060A patent/KR870000246B1/ko not_active Expired
- 1983-03-16 NZ NZ203592A patent/NZ203592A/en unknown
- 1983-03-16 RO RO110354A patent/RO87596B/ro unknown
- 1983-03-16 PT PT76398A patent/PT76398B/pt unknown
- 1983-03-16 ZA ZA831840A patent/ZA831840B/xx unknown
- 1983-03-16 GB GB08307289A patent/GB2117380B/en not_active Expired
- 1983-03-16 JP JP58042527A patent/JPS58167525A/ja active Pending
- 1983-03-16 DD DD83248846A patent/DD207903A5/de unknown
- 1983-03-16 PL PL24104983A patent/PL241049A1/xx unknown
- 1983-03-16 CS CS831829A patent/CS240955B2/cs unknown
-
1987
- 1987-12-30 MY MY115/87A patent/MY8700115A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2117380A (en) | 1983-10-12 |
| EP0089330B1 (de) | 1987-04-22 |
| PT76398A (en) | 1983-04-01 |
| NZ203592A (en) | 1986-02-21 |
| DE3371068D1 (en) | 1987-05-27 |
| RO87596A (ro) | 1985-08-31 |
| EP0089330A2 (de) | 1983-09-21 |
| CS182983A2 (en) | 1985-06-13 |
| KR870000246B1 (ko) | 1987-02-21 |
| GB8307289D0 (en) | 1983-04-20 |
| AU1249283A (en) | 1983-09-22 |
| RO87596B (ro) | 1985-09-01 |
| ZA831840B (en) | 1983-12-28 |
| PT76398B (en) | 1985-12-05 |
| KR840004058A (ko) | 1984-10-06 |
| GB2117380B (en) | 1986-04-23 |
| ATE26698T1 (de) | 1987-05-15 |
| HU189673B (en) | 1986-07-28 |
| DD207903A5 (de) | 1984-03-21 |
| MY8700115A (en) | 1987-12-31 |
| EP0089330A3 (en) | 1985-03-27 |
| PL241049A1 (en) | 1984-01-30 |
| JPS58167525A (ja) | 1983-10-03 |
| AU562361B2 (en) | 1987-06-11 |
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