CS267501B1 - Dithioderivatives of 0-carbamoylmethyl-4-hydroxybutanesulphonic acid and method of their preparation - Google Patents
Dithioderivatives of 0-carbamoylmethyl-4-hydroxybutanesulphonic acid and method of their preparation Download PDFInfo
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- CS267501B1 CS267501B1 CS863069A CS306986A CS267501B1 CS 267501 B1 CS267501 B1 CS 267501B1 CS 863069 A CS863069 A CS 863069A CS 306986 A CS306986 A CS 306986A CS 267501 B1 CS267501 B1 CS 267501B1
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- carbon atoms
- general formula
- hydrogen
- preparation
- carbamoylmethyl
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- 239000002253 acid Substances 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 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 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000011734 sodium Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011591 potassium Substances 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- -1 nitro- Chemical class 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 3
- 229910052802 copper Inorganic materials 0.000 abstract description 3
- 239000010949 copper Substances 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 3
- 230000008020 evaporation Effects 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 101100016026 Drosophila melanogaster GstE14 gene Proteins 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical class CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 1
- YEGPVWSPNYPPIK-UHFFFAOYSA-N 4-hydroxybutane-1-sulfonic acid Chemical compound OCCCCS(O)(=O)=O YEGPVWSPNYPPIK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 235000013522 vodka Nutrition 0.000 description 1
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- Electroplating And Plating Baths Therefor (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Jodná se o látky obecného vzorce R—CIL,—0-(01^ )Z(S0"Me + , kdo Mo Jc sodík, draslík nebo vodík a R jo zbytok obecného vzorce Ha R^-S-N=C-S- nebo líh R-r\'-C=S-S-, vo kterém R^ je o-disubstituované aromatioké jádro s počtem atomů uhliku 6 až 20 noho lioterooronatic^.é jádro s počtom uhlíků 3 a£ 10 a R~ a R-> jsou stejné nebo různé alkylové zbytky o počtu atonrů uhlíku 1 až 6 nebo vodík. Jsou to nové nalezené látky, ktoré jc možné izolovat odpařením nebo přímo užit vo formě reedičního roztoku jako přísada do galvaniokých mědících kysolých lázní.These are substances of the general formula R — CIL, —0- (01 ^) Z (S0 "Me +, who Mo Jc sodium, potassium or hydrogen and R10 is a radical of formula (IIa) R 1 -S-N = C-S- or alcohol R 1 -R = C-S-S- in which R 6 is o-disubstituted aromatic nucleus with number carbon atoms of 6 to 20 carbon atoms a core with a carbon number of 3 and £ 10 and R 2 and R 6 are the same or different alkyl carbon atoms 1 to 6 or hydrogen. They are new found substances which can be isolated by evaporation or directly used in the form of a re-edition solution as an additive to galvans copper acid baths.
Description
Vynález no týká dlthlodorlvátů O-kArbaraoylraothyl-if-hydxOXj’butnnsuJTonovi kyseliny a způsobu JoJioli přípravy.The present invention relates to O-carbamoyl-butyl-.alpha.-hydroxy-.alpha.-butyric acid derivatives and to a process for the preparation.
Dyly nnlozony novó látky oboonóho vzorce I n-ClLj-O-ÍClLj^SO-Ho·*· (I) kdo Mo Jo sedák, draslík nobo vodák a R Jo zbytek oboonóho vzox*co Ila nobo líhDyly nnlozony new substances of obone formula I n-ClLj-O-ÍClLj ^ SO-Ho · * · (I) who Mo Jo sedák, potassium or vodka and R Jo the rest of oboonó vzox * co Ila nobo alcohol
(Ilo) (IH>) vo ktorórn R Jo o-disubstituovaná ar· o matické Jádro a počtem atotnů uhlíku 6 až 20 nobo hotoroaromatické Jádro s počtem uhlíků 3 až 10, sírou, dusíkem nobo leyslíkom obsahující připadnu halo-, nitro-, sulfo-, hydroxy-, amino-, n/nobo morkaptoskupiny nobo alkyl^n o poutu atomů uhlíku 2 až 20, R , R, Jsou stojné nebo nižné alkylová zbytky o počtu atomu uJilíku 1 až 6 nobo vodák.(Ilo) (IH>) in which R Jo o-disubstituted ar · Nucleic nucleus with a number of carbon atoms 6 to 20 or hotoroaromatic nucleus with a number of carbons 3 to 10, sulfur, nitrogen or oxygen containing halo-, nitro-, sulfo -, hydroxy-, amino-, n / or morkapto groups or alkyl groups of carbon atoms 2 to 20, R, R, are identical or lower alkyl residues with the number of carbon atoms 1 to 6 or hydrogen.
Úvodené látky dosud nebyly v literatuře popsány. Jsou známy pouzo obdobné deriváty á-hydroxypropansulfonová kyseliny, jejichž syntÓ7-a vyžaduje užití vysoce Icrtrcinogonního |,3-propansulfonu, což Jo toolinicky neúnosná. Proto bylo hlodáno, zda obdobná účinky (leštící přísada do kyselých, galvanických mědících lázní) nomají i deriváty získaná z nokancorogonnáho 1,U-butansuXfonu. Podstata způsobu výroby dithioderivátú 0-karbamoyl-/<-hydroxybutanouJl?ono\-ých kyselin podlo vynálezu spočívá v tom, že se na dithioderiváty obecného vzorec R-II nebo R-R, kdo R Jo radikál obecného vzorce Ha nobo lib působí v přítomnosti báze ϊ,ά-butansulTonom, popřípadě i fomtaldohydem ve vodu a/nobo alifatickém alkoholu s počtem atomů uhlíků 1 až 6 j>ři teplotu 10 až 120 °C po dobu 0,05 až 5 hodin.Introductory substances have not yet been described in the literature. Only similar α-hydroxypropanesulfonic acid derivatives are known, the synthesis of which requires the use of highly tertiary pathogenic 1,3-propanesulfone, which is toolinically unbearable. Therefore, it was investigated whether similar effects (polishing additive for acidic, galvanic copper baths) are exemplified by derivatives obtained from nokancorogonná 1, U-butanesulfone. The process for the preparation of the dithioderivatives of O-carbamoyl- / .beta.-hydroxybutanoic acid according to the invention consists in that the dithioderivatives of the general formula R-II or RR are treated with a radical of the formula Ha nobo lib in the presence of a base. , α-butanesulfonone, optionally also with phthaldehyde in water and / or an aliphatic alcohol having 1 to 6 carbon atoms at a temperature of 10 to 120 ° C for 0.05 to 5 hours.
Tyto látky jsou pevná, bílá sloučeniny amorfního charakteru, která lze Jen volrai nedokonalo krystalovat z etanolu. Kyselinu nolze izolovat v čistém stavu, soli Izo z roztoku po odpaření izolovat a stanovit například infračervenými spoktiy nobo pomocí NMR spektry. Jsou notavitelná a noclxaruktďizovatolnó běžnými metodami.These substances are solid, white compounds of amorphous character which can be imperfectly crystallized from ethanol only. The acid can be isolated in the pure state, the Izo salts isolated from the solution after evaporation and determined, for example, by infrared spectra or by NMR spectra. They are removable and noclxaruktďizovatolnó by conventional methods.
Jako výchozí látky slouží bučí to t raníky 1 tlil urdiaulf Id, dlalkyldithlokarbamovú kyselina ui její soli, v připadá dialkyldithiokoxbamové kyseliny reakcí v oxidačním prostředí muže totraalkylthiur&rodleulfid intermediálně vznikat a limed dálo reagovat, Derivátom dithiokarbomové kyseliny Je i 2-morka.ptobonzthiazol, ktoxý kiúŽo onnloficky reagovat, Reakce probíhá v přítomnosti hydroxylových iontů ve vodném nobo vodnáalkoholiokám prostřodá. Produkt může být bu3 izolován oixxtmýra odpařením nebo i přímo užit ve formě roakčního roztoku Jako přísada do galvanických mědících kyselých lázní. Příklad 1 g Ν,Ν,Ν',Η-totramothylthiuramdisulfldu se smíeliá so 100 ml etonolu, 2 1 vody a 25 £ hydroxidu sodného a mícliů se 3 hodiny při teplotu άθ °C. Pak so přidá postupně 26 g formaldohydu a 82 g t ,^-butansulfonu a zahřívá se na 100 °C jednu hodinu. Vzniklý roztok 0-(N,N-dimothylditliiokarbameylmothyl-)^-hydroxybutansuironanu sodného.The starting materials used are dialkyldithiocarbamic acid and its salts. The reaction takes place in the presence of hydroxyl ions in aqueous or aqueous alcohols. The product can either be isolated by evaporation or even used directly in the form of a fractional solution as an additive in galvanic copper acid baths. Example 1 g of Ν, Ν, Ν ', Η-totramothylthiuram disulfide are mixed with 100 ml of ethanol, 2 l of water and 25% of sodium hydroxide and milled for 3 hours at άθ ° C. 26 g of formaldehyde and 82 g of t-butanesulfone are then added in succession and heated at 100 DEG C. for one hour. The resulting solution of sodium O- (N, N-dimethyldithiocarbameylmethyl) -N-hydroxybutanesuironate.
CS 267 501 BlCS 267 501 Bl
Příklad 2Example 2
100 c 2-racrkaptobenzthiazolu se smíchá, e 1,5 1 vody, 25 e hydroxidu sodného a míchá se pří teplotě fy$ °C 2 hodiny. Pak se přidá postupné 20 e paraformaldehydu a 82 g 1,4—butansulfonu a zahřívá se 3° minut na 90 °C. Vzniklý roztok O-(S-2-raerkaptobonztIiiazolylmothyl-)4-hydroxybutansulfonanu sodného, který byl ve vakuu při teplotě 50 °C odpařen k suchu a odparek rozmíchán s malým množstvím studeného etanolu. Po sušení při 40 °C byl získán bílý, notavitelný prážek.100 c of 2-raccaptobenzothiazole are mixed with 1.5 l of water, 25 e of sodium hydroxide and stirred at room temperature for 2 hours. 20 g of paraformaldehyde and 82 g of 1,4-butanesulfone are then added successively and the mixture is heated at 90 DEG C. for 3 minutes. The resulting solution of sodium O- (S-2-mercaptobenzothiazolylmethyl) -4-hydroxybutanesulfonate was evaporated to dryness in vacuo at 50 ° C and the residue was stirred with a small amount of cold ethanol. After drying at 40 ° C, a white, meltable powder was obtained.
Příklad 3 a N,N,NfN-tetrahexylthiuramidisulfidu se smíchá se 1000 ml otanolu a 3° β hydroxidu sodného a míoliá>so 2,5 hodiny při teplotě 5® °C· Pak ee přidají postupné 2 1 vody, 23 g parafortnaldehydu a 85 6 1,4-butansulfonu a zahřívá se 2 hodiny na 95 °C. Vzniklý roztok 0-(N,N-diethyldithiokarbamoylraethyl-)4-hydroxybutansulfonanu. sodného můžo být přímo dále užíván.Example 3 a N, N, NfN-tetrahexylthiuramidisulfide is mixed with 1000 ml of otanol and 3 ° β of sodium hydroxide and milled for 2.5 hours at 5 ° C. Then 2 l of water, 23 g of parafortnaldehyde and 85 6 of 1,4-butanesulfone and heated at 95 ° C for 2 hours. The resulting solution of O- (N, N-diethyldithiocarbamoylraethyl-) 4-hydroxybutanesulfonate. sodium can be used directly.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863069A CS267501B1 (en) | 1986-04-28 | 1986-04-28 | Dithioderivatives of 0-carbamoylmethyl-4-hydroxybutanesulphonic acid and method of their preparation |
| CS87555A CS267515B1 (en) | 1986-04-28 | 1987-01-28 | Lustre forming admixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863069A CS267501B1 (en) | 1986-04-28 | 1986-04-28 | Dithioderivatives of 0-carbamoylmethyl-4-hydroxybutanesulphonic acid and method of their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS306986A1 CS306986A1 (en) | 1989-06-13 |
| CS267501B1 true CS267501B1 (en) | 1990-02-12 |
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ID=5369699
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863069A CS267501B1 (en) | 1986-04-28 | 1986-04-28 | Dithioderivatives of 0-carbamoylmethyl-4-hydroxybutanesulphonic acid and method of their preparation |
| CS87555A CS267515B1 (en) | 1986-04-28 | 1987-01-28 | Lustre forming admixture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS87555A CS267515B1 (en) | 1986-04-28 | 1987-01-28 | Lustre forming admixture |
Country Status (1)
| Country | Link |
|---|---|
| CS (2) | CS267501B1 (en) |
-
1986
- 1986-04-28 CS CS863069A patent/CS267501B1/en unknown
-
1987
- 1987-01-28 CS CS87555A patent/CS267515B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS55587A1 (en) | 1989-06-13 |
| CS267515B1 (en) | 1990-02-12 |
| CS306986A1 (en) | 1989-06-13 |
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