PL53375B1 - - Google Patents
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- PL53375B1 PL53375B1 PL103361A PL10336163A PL53375B1 PL 53375 B1 PL53375 B1 PL 53375B1 PL 103361 A PL103361 A PL 103361A PL 10336163 A PL10336163 A PL 10336163A PL 53375 B1 PL53375 B1 PL 53375B1
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- hal
- carbon atoms
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- oxygen
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- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 239000012990 dithiocarbamate Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- -1 1 - [(2-isothiocyanatoacetyl) amino] - 4 - isothiocyanatobenzene Chemical compound 0.000 description 1
- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 1
- ZJYRREQOICKGAM-UHFFFAOYSA-N 2-amino-N-(4-aminophenyl)acetamide dihydrochloride Chemical compound Cl.Cl.NCC(=O)NC1=CC=C(N)C=C1 ZJYRREQOICKGAM-UHFFFAOYSA-N 0.000 description 1
- PLWCDUKITJQNKM-UHFFFAOYSA-N 2-amino-n'-phenylacetohydrazide Chemical compound NCC(=O)NNC1=CC=CC=C1 PLWCDUKITJQNKM-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
Description
Przyklad XV. Postepujac jak w przykla- 35 dzie VI, lecz wychodzac z 2,4 g dwuchlorowodor- ku 4-[(2-aminoacetylo)-amino]-aniliny, 4,2 g we¬ glanu wapniowego i 2,5 g tiofosgenu otrzymuje sie po przeprowadzonej chromatografii na tlenku glinowym w chlorku metylenu i nastepnej kry- 40 stalizacji z octanu etylu 0,3 g 1-[(2-izotiocyjania- noacetylo) - amino] - 4 - izotiocyjanianobenzenu, o temperaturze topnienia 186°.W celu wytworzenia 4-[(2-aminoacetylo)-amino]- --aniliny stosowanej jako produkt wyjsciowy dzia- 45 la sie chlorkiem 2-ftalimidoacetylu na 4-nitro- aniline, uwodornia otrzymany produkt w dwu- metyloformamidzie w obecnosci niklu Raney'a w temperaturze 20° pod cisnieniem 10 barów do 4-K2-ftalimidoacetylo)-amino]-aniliny, która 50 odftalimiduje sie za pomoca wodzianu hydra¬ zyny. PL
Claims (1)
1. Zastrzezenie patentowe 55 Sposób wytwarzania nowych izotiocyjanianów o wzorze ogólnym 1, w którym A oznacza wia¬ zanie pojedyncze albo rodnik alkilenowy prosty lub rozgaleziony o 1—6 atomach wegla i ewen¬ tualnie polaczony z rdzeniem fenylowym poprzez $o atom tlenu lub siarki albo ugrupowanie sulfo- nylowe, A' (w pozycji orto lub para w stosun¬ ku do A) oznacza rodnik alkilenowy prosty lub rozgaleziony o 1—6 atomach wegla i ewentualnie polaczony z rdzeniem fenylowym poprzez atom 65 tlenu lub siarki albo ugrupowanie sulfonylowe,53375 a R oznacza atom wodoru lub chlorowca albo rodnik alkilowy, alkoksylowy lub alkilotio- o 1—4 atomach wegla, hydroksylowy, nitrowy, cyjano¬ wy albo trój fluor omety Iowy, znamienny tym, ze dziala sie dwuamina o wzorze 2, w którym A, A' i R maja znaczenie wyzej podane na tiofos- gen, albo na dwusiarczek wegla, przy czym re- 8 akcje prowadzi sie wtedy w obecnosci amoniaku lub wodorotlenku alkalicznego, po czym rozkla¬ da otrzymany dwutiokarbaminian, albo sola me¬ taliczna kwasu tiocyjanowego dziala sie na chlo¬ rowcowana pochodna o wzorze 4, w którym Hal oznacza atom chlorowca, a pozostale symbole ma¬ ja znaczenie wyzej podane. -A-NCS SCN-A WZÓJll A'-J% WZÓR 2 v MS-SC-HN-A' WZGB3 Hal-A' -A-NH-CS-SM ^ . // -A-Hal WZÓB/t WDA-l. Zam. 425/67. Nakl. 310 egz. PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL53375B1 true PL53375B1 (pl) | 1967-04-25 |
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