CS271148B1 - Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation - Google Patents
Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation Download PDFInfo
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- CS271148B1 CS271148B1 CS887062A CS706288A CS271148B1 CS 271148 B1 CS271148 B1 CS 271148B1 CS 887062 A CS887062 A CS 887062A CS 706288 A CS706288 A CS 706288A CS 271148 B1 CS271148 B1 CS 271148B1
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- Czechoslovakia
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- general formula
- carbamoyl
- dithioderivatives
- carbon atoms
- hydrogen
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- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- BDQHVRMGLCXJQJ-UHFFFAOYSA-N 1-amino-5-hydroxy-1-oxopentane-2-sulfonic acid Chemical class C(N)(=O)C(CCCO)S(=O)(=O)O BDQHVRMGLCXJQJ-UHFFFAOYSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011591 potassium Substances 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- OLCLIWVKEDRSFW-UHFFFAOYSA-N 5-amino-5-oxopentane-1-sulfonic acid Chemical class NC(=O)CCCCS(O)(=O)=O OLCLIWVKEDRSFW-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052802 copper Inorganic materials 0.000 abstract description 3
- 239000010949 copper Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 231100001223 noncarcinogenic Toxicity 0.000 abstract description 2
- 238000005498 polishing Methods 0.000 abstract description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- -1 hydroxyl ions Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 231100000315 carcinogenic Toxicity 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001590 oxidative effect Effects 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Vynález se týká dithioderivátu karbamoyl-4-butansulfonové kyseliny a jejich derivátu a způsobu jejich přípravy. Byly nalezeny nové látky obecného vzorce IThe present invention relates to a carbamoyl-4-butanesulfonic acid dithioderivative and a derivative thereof, and to a process for their preparation. New compounds of formula I have been found
R-(CH2)^SO^Me* (I) , kde Me je sodík, draslík nebo vodík a R je zbytek obecného vzorce Ila nebo libR - (CH 2 ) 2 SO 4 Me * (I), wherein Me is sodium, potassium or hydrogen and R is a radical of formula (IIa) or (IIb)
ve kterém R1 je o-disubstituované aromatické jádro s počtem atomů uhlíku 6 až 20 nebo heteroaromatické jádro s počtem uhlíků 2 až 10, sírou, dusíkem nebo kyslíkem, obsahující případně halo-, sulfo-, hydroxy-, amino- a/nebo merkaptoskupiny nebo alkylen o počtu ato2 3 mů uhlíku 2 až 20, R , R jsou stejné nebo různé alkylové zbytky o počtu atomů uhlíku 1 až 6 nebo vodík.wherein R 1 is an o-disubstituted aromatic nucleus having a carbon number of 6 to 20 or a heteroaromatic nucleus having a carbon number of 2 to 10, sulfur, nitrogen or oxygen, optionally containing halo-, sulfo-, hydroxy-, amino- and / or mercapto groups or an alkylene of from 3 to 10 carbon atoms of 2 to 20, R, R are the same or different alkyl radicals of 1 to 6 carbon atoms or hydrogen.
Uvedené látky dosud nebyly v literatuře popsány. Jsou známy pouze obdobné derivátyThese substances have not been described in the literature yet. Only similar derivatives are known
4-hydroxypropansulfonové kyseliny, jejichž syntéza vyžaduje užití vysoce karcinogenního4-hydroxypropanesulfonic acids whose synthesis requires the use of a highly carcinogenic one
1.3- propansulfonu , což je technicky neúnosné. Proto bylo hledáno, zda obdobné účinky (leš- ' ticí přísada do kyselých galvanických mědících lázní) nemají i deriváty, získané z nekancerogenního 1, 4-butansulfonu.1.3-propanesulfone, which is technically unacceptable. It has therefore been sought whether derivatives obtained from non-cancerogenic 1,4-butanesulfone have similar effects (polishing additive for acidic galvanic copper baths).
Podstata způsobu výroby dithioderivátů karbamoyl-4-butansulfonových kyselin a jejich derivátů podle vynálezu spočívá v tom, že se na dithioderiváty obecného vzorce R- nebo R-R, kde R je radikál obecného vzorce Ha nebo lib působí v přítomnosti báze 1,4-butansulfonu ve vodě a/nebo alifatického alkoholu s počtem atomů uhlíku 1 až 6 při teplotě 10 až 120 °C, a to po dobu 0,05 až 5 hodin.The process for the preparation of carbamoyl-4-butanesulfonic acid dithioderivatives and their derivatives according to the invention consists in treating dithioderivatives of the formula R- or RR, where R is a radical of the formula IIa or IIb in the presence of 1,4-butanesulfone base in water and / or an aliphatic alcohol having a carbon number of 1 to 6 at a temperature of 10 to 120 ° C for 0.05 to 5 hours.
Tyto látky jsou pevné, bílé sloučeniny amorfního charakteru, které lze jen velmi nedokonale krystalovat z ethanolu. Kyselinu nelze izolovat v čistém stavu, soli lze z roztoku po odpaření izolovat a stanovit například infračervenými spektry nebo pomocí NMR spekter. Jsou nestanovitelné a necharakterizovatelné běžnými metodami.These substances are solid, white compounds of amorphous character which can only be crystallized very poorly from ethanol. The acid cannot be isolated in its pure state, the salts can be isolated from the solution after evaporation and determined, for example, by infrared or NMR spectra. They are undetectable and not characterized by conventional methods.
Jako výchozí látky slouží bud tetraall^ylthiuramdisulfid, dialkyldithiokarbamová kyselina či její soli, v případě dialkyldithiokarbamové kyseliny reakcí v oxidačním prostředí může tetraalkylthiuramdisulfid intermediálně vznikat a ihned dále reagovat. Derivátem dithiokarbamové kyseliny je i 2-merkaptobenzthiazol, který může analogicky reagovat. Reakce probíhá v přítomnosti hydroxylových iontů ve vodném nebo vodněalkoholickém prostředí. Produkt může být bud izolován opatrným odpařením, nebo i přímo užit ve formě reakčního roztoku jako přísada do galvanických mědících kyselých lázní.Tetraalkylthiuram disulfide, dialkyldithiocarbamic acid or salts thereof may be used as starting materials, in the case of dialkyldithiocarbamic acid by reaction in an oxidizing medium, tetraalkylthiuram disulfide may be formed intermittently and react immediately. The dithiocarbamic acid derivative is also 2-mercaptobenzthiazole, which can react analogously. The reaction takes place in the presence of hydroxyl ions in an aqueous or aqueous-alcoholic medium. The product can either be isolated by careful evaporation or even directly used as a reaction solution as an additive to the galvanic copper acid bath.
Příklad 1 1 g Ν,Ν,Ν’Ν’- tetramethylthiuramdisulfidu se smíchá se 100 ml etanolu, 2 1 vody a g hydroxidu sodného a míchá se 3 hodiny při teplotě 40 °C. Pak se přidá postupně 82 g u EXAMPLE 1 1 g of tetramethylthiuram disulfide was mixed with 100 ml of ethanol, 2 l of water and sodium hydroxide and stirred at 40 DEG C. for 3 hours. Then was added successively 82 g in
1.4- butansulfonu a zahřívá se na 100 °C jednu hodinu. Vzniklý roztok N,N-dimethyldithiokarbamoyl-4-butansulfonanu sodného může být přímo dále užíván.1,4-butanesulfone and heated to 100 ° C for one hour. The resulting sodium N, N-dimethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.
Příklad 2Example 2
100 g 2-merkaptobenzthiazolu se míchá s 1,5 1 vody, 25 g hydroxidu sodného a míchá se při teplotě 45 °C 2 hodiny. Potom se přidá postupně 82 g 1,4-butansulfonu a zahřívá se 30 minut na 90 °C. Vzniklý roztok 2-merkaptobenzthiazolyl-4-butansulfonanu sodného, který byl ve vakuu při teplotě 50 °c odpařen к suchu a odparek rozmíchán s malým množstvím stu^ děného ethanolu. Po sušení při 40 °C byl získán bílý nestanovitelný prášek.100 g of 2-mercaptobenzthiazole are stirred with 1.5 l of water, 25 g of sodium hydroxide and stirred at 45 DEG C. for 2 hours. Subsequently, 82 g of 1,4-butanesulfone are added successively and heated to 90 ° C for 30 minutes. The resulting solution of sodium 2-mercaptobenzthiazolyl-4-butanesulfonate was evaporated to dryness in vacuo at 50 ° C and the residue was stirred with a little cold ethanol. After drying at 40 ° C, a white, non-determinable powder was obtained.
Příklad 3 · g Ν,Ν,Ν’Ν’-tetraethylthioramidisulfidu se smíchá se 1 000 ml ethanolu a 30 g hydroxidu sodného a míchá se 2,5 hodiny při teplotě 50 °C. Pak se přidají postupně 2 1 vody,Example 3 · g Ν, Ν, Ν’Ν-tetraethylthioramide disulfide is mixed with 1000 ml ethanol and 30 g sodium hydroxide and stirred for 2.5 hours at 50 ° C. Then add 2 liters of water,
CS 271 148 Bl g 1,4-butansulfonu a zahřívá se 2 hodiny na 95 °C. Vzniklý roztok N,N-diethyldithiokarbamoyl-4-butansulfonanu sodného může být přímo dále užíván.CS 271 148 B1 g of 1,4-butanesulfone and heated at 95 ° C for 2 hours. The resulting sodium N, N-diethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.
Příklad 4 g Ν,Ν-diethyldithiokarbaminanu draselného se smíchá s 1,5 1 vody a míchá se při teplotě 25 °C půl hodiny. Potom se přidá 83 g 1,4-butansulfonu a zahřívá se za míchání 1 hodinu na 90 °C. Vzniklý roztok N,N-diethyldithiokarbamoyl-4-butansulfonanu draselného může být přímo dále užíván.Example 4 Potassium Ν, Ν-diethyldithiocarbaminate (4 g) was mixed with 1.5 L of water and stirred at 25 ° C for half an hour. 83 g of 1,4-butanesulfone are then added and heated to 90 ° C with stirring for 1 hour. The resulting potassium N, N-diethyldithiocarbamoyl-4-butanesulfonate solution can be used directly.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887062A CS271148B1 (en) | 1988-10-20 | 1988-10-20 | Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887062A CS271148B1 (en) | 1988-10-20 | 1988-10-20 | Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation |
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| Publication Number | Publication Date |
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| CS706288A1 CS706288A1 (en) | 1990-01-12 |
| CS271148B1 true CS271148B1 (en) | 1990-08-14 |
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| CS887062A CS271148B1 (en) | 1988-10-20 | 1988-10-20 | Dithioderivatives of carbamoyl-4-hydroxybutanesulphonic acid and method of its preparation |
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| CN119176779B (en) * | 2024-11-25 | 2025-07-08 | 江西华创新材有限公司 | Preparation method and application of five-membered nitrogen heterocyclic monothiopropane sulfonate |
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1988
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