DE1543933A1 - Nitrosulfide und Verfahren zu ihrer Herstellung - Google Patents
Nitrosulfide und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1543933A1 DE1543933A1 DE19661543933 DE1543933A DE1543933A1 DE 1543933 A1 DE1543933 A1 DE 1543933A1 DE 19661543933 DE19661543933 DE 19661543933 DE 1543933 A DE1543933 A DE 1543933A DE 1543933 A1 DE1543933 A1 DE 1543933A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- acetanilide
- nitrostyrene
- nitro
- aminobenzaldehyde
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 6
- YNDUPGQMECPWKD-UHFFFAOYSA-N [O-][N+](=O)S[N+]([O-])=O Chemical class [O-][N+](=O)S[N+]([O-])=O YNDUPGQMECPWKD-UHFFFAOYSA-N 0.000 title claims description 5
- 229960001413 acetanilide Drugs 0.000 claims description 20
- -1 carboxylic acid anhydride Acetic anhydride Chemical class 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 5
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- DAKOAPKOFYSAOU-UHFFFAOYSA-N NC1=C(C=O)C=CC=C1.NC1=CC=C(C=O)C=C1 Chemical compound NC1=C(C=O)C=CC=C1.NC1=CC=C(C=O)C=C1 DAKOAPKOFYSAOU-UHFFFAOYSA-N 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- AXWKRUFUAGYTHB-UHFFFAOYSA-N 2-butylbenzenethiol Chemical compound CCCCC1=CC=CC=C1S AXWKRUFUAGYTHB-UHFFFAOYSA-N 0.000 description 3
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QOFYCZQQGPFMRL-UHFFFAOYSA-N n-(4-formylphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(C=O)C=C1 QOFYCZQQGPFMRL-UHFFFAOYSA-N 0.000 description 2
- BMUMTWKTXISIKR-UHFFFAOYSA-N n-(4-formylphenyl)propanamide Chemical compound CCC(=O)NC1=CC=C(C=O)C=C1 BMUMTWKTXISIKR-UHFFFAOYSA-N 0.000 description 2
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NDKJATAIMQKTPM-UHFFFAOYSA-N 2,3-dimethylbenzenethiol Chemical compound CC1=CC=CC(S)=C1C NDKJATAIMQKTPM-UHFFFAOYSA-N 0.000 description 1
- ABROBCBIIWHVNS-UHFFFAOYSA-N 2-Ethylbenzenethiol Chemical compound CCC1=CC=CC=C1S ABROBCBIIWHVNS-UHFFFAOYSA-N 0.000 description 1
- LPAXQAHKKBQAEP-UHFFFAOYSA-N 2-methyl-5-propan-2-ylbenzenethiol Chemical compound CC(C)C1=CC=C(C)C(S)=C1 LPAXQAHKKBQAEP-UHFFFAOYSA-N 0.000 description 1
- JPNXREVRYWWBDG-UHFFFAOYSA-N 2-propylbenzenethiol Chemical compound CCCC1=CC=CC=C1S JPNXREVRYWWBDG-UHFFFAOYSA-N 0.000 description 1
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 1
- WWQQPHUHTAZWDH-UHFFFAOYSA-N 4-ethylbenzenethiol Chemical compound CCC1=CC=C(S)C=C1 WWQQPHUHTAZWDH-UHFFFAOYSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- CEELNENBAZWPRU-UHFFFAOYSA-N C(CCC)C=1C=C(C=C(C1)CC)S Chemical compound C(CCC)C=1C=C(C=C(C1)CC)S CEELNENBAZWPRU-UHFFFAOYSA-N 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 241000191984 Staphylococcus haemolyticus Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- OWMJAQBUFVTERI-UHFFFAOYSA-N n-(2-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1C=O OWMJAQBUFVTERI-UHFFFAOYSA-N 0.000 description 1
- KBKWZUVMKBNTFP-UHFFFAOYSA-N n-(3-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=C1 KBKWZUVMKBNTFP-UHFFFAOYSA-N 0.000 description 1
- BWLIIZFNXSJVLW-UHFFFAOYSA-N n-[4-(2-nitroethenyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C=C[N+]([O-])=O)C=C1 BWLIIZFNXSJVLW-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US509409A US3376340A (en) | 1965-11-23 | 1965-11-23 | Substituted carboxanilides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543933A1 true DE1543933A1 (de) | 1970-02-05 |
Family
ID=24026548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543933 Pending DE1543933A1 (de) | 1965-11-23 | 1966-11-16 | Nitrosulfide und Verfahren zu ihrer Herstellung |
Country Status (7)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2901508A (en) * | 1957-05-02 | 1959-08-25 | Upjohn Co | Organic compounds and process |
-
1965
- 1965-11-23 US US509409A patent/US3376340A/en not_active Expired - Lifetime
-
1966
- 1966-11-02 IL IL26792A patent/IL26792A/xx unknown
- 1966-11-03 GB GB49390/66A patent/GB1156827A/en not_active Expired
- 1966-11-16 DE DE19661543933 patent/DE1543933A1/de active Pending
- 1966-11-17 CH CH1654766A patent/CH467253A/de unknown
- 1966-11-22 NL NL6616410A patent/NL6616410A/xx unknown
- 1966-11-22 FR FR84473A patent/FR1501424A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3376340A (en) | 1968-04-02 |
| GB1156827A (en) | 1969-07-02 |
| CH467253A (de) | 1969-01-15 |
| NL6616410A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-24 |
| IL26792A (en) | 1970-09-17 |
| FR1501424A (fr) | 1967-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1645964A1 (de) | Oxazepine und Thiazepine | |
| DE69619230T2 (de) | Oxidatives verfahren zur herstellung von narwedin-derivaten | |
| DE1543933A1 (de) | Nitrosulfide und Verfahren zu ihrer Herstellung | |
| CH520117A (de) | Verfahren zur Herstellung von basisch substituierten Oximen des 5H-Dibenzo-(a,d)-10,11-dihydro-cyclohepten-5-ons | |
| AT330169B (de) | Verfahren zur herstellung neuer oxindole und ihrer salze | |
| AT203002B (de) | Verfahren zur Herstellung von neuen, heterocyclisch substituierten Pyrazolonderivaten | |
| CH512500A (de) | Verfahren zur Herstellung von Phenazin-Derivaten | |
| DE951630C (de) | Verfahren zur Herstellung von in 20 (22)-Stellung ungesaettigten 22-tertiaer-Aminobisnorcholanen | |
| AT219613B (de) | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen und deren Salzen | |
| DE1814625C (de) | Zimtsaureamide | |
| AT229878B (de) | Verfahren zur Herstellung von neuen Thioxanthen-Derivaten | |
| AT274802B (de) | Verfahren zur Herstellung von Indolderivaten | |
| AT272350B (de) | Verfahren zur Herstellung von 2,3-Dihydro-1H-1,4-benzodiazepinen und von Säureadditionssalzen dieser Verbindungen | |
| AT211818B (de) | Verfahren zur Herstellung von neuen Aryloxyessigsäureamiden | |
| DE1620705C3 (de) | Verfahren zur Herstellung von substituierten 2-Alkoxy-carbonylmethyl-1,4,6,7-tetrahydro-11bH-benzo-(a)chinolizinen | |
| AT300785B (de) | Verfahren zur Herstellung von neuen 1-Β-Phenylpropioloyl-3-indolylessigsäurederivaten | |
| AT203015B (de) | Verfahren zur Herstellung von neuen 1-(p-Butoxyphenyl)-3-(p-pyridylphenyl)-2-thioharnstoffen | |
| DE1670152A1 (de) | Verfahren zur Herstellung N-substituierter Granatanoltropasaeureester | |
| AT211819B (de) | Verfahren zur Herstellung von neuen Aryloxyessigsäureamiden | |
| AT223202B (de) | Verfahren zur Herstellung von neuen Phenothiazinderivaten | |
| DE1620536C (de) | Verfahren zur Herstellung von alpha Pyrrolidinoketonen und ihren Salzen | |
| AT283364B (de) | Verfahren zur Herstellung neuer Zimtsäureamide | |
| AT206900B (de) | Verfahren zur Herstellung von neuen 1-Amino-2,4-dioxo-azetidin-Derivaten | |
| AT366370B (de) | Verfahren zur herstellung von neuen benz(g) isochinolinderivaten | |
| DE1190464B (de) | Verfahren zur Herstellung von Pyridinderivaten |