CS267501B1 - Dithiodorivatives of O-carbamoylmethyl-f-hydroxybutanesulfonic acid and a process for their preparation - Google Patents

Abstract

These are substances of the general formula R—CIL,—0-(01^ )Z(S0"Me + , where Mo is sodium, potassium or hydrogen and R is a residue of the general formula Ha R^-S-N=C-S- or an alcohol R-r\'-C=S-S-, in which R^ is an o-disubstituted aromatic nucleus with a number of carbon atoms of 6 to 20 or a lioteroronatic nucleus with a number of carbon atoms of 3 to £ 10 and R~ and R-> are the same or different alkyl residues with a number of carbon atoms of 1 to 6 or hydrogen. They are newly discovered substances that can be isolated by evaporation or directly used in the form of a redistribution solution as an additive to galvanic copper acid baths.

Description

The present invention relates to O-carbamoyl-butyl-.alpha.-hydroxy-.alpha.-butyric acid derivatives and to a process for the preparation.

Dyly 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>) 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.

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.

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.

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 Bl

Example 2

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.

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)

O-Carbamoylmethyl-4-hydroxybutanesulfonic acid dimethyl derivatives of general formula I. R-Cn ₂ -O- (CH 2 is SO 2 Mo * (I) who is not sodium, potassium or hydrogen and R is a residue of formula IIa or Hb (Ha) wherein the o-disubstituted aromatic nucleus having 6 to 20 carbon atoms or a heteroaromatic nucleus having 3 to 10 carbon numbers, sulfur, nitrogen or oxygen containing optionally halo-, nitro-, sulfo-, hydroxy-, amino-, and / or mercapto group 3 alkylene having a carbon number of 2 to -20, R, R 1 are the same or different alkyl radicals having a carbon number of 1 to 6 or hydrogen, 2. A process for the preparation of dithio derivatives of O-carbamoyl-4-hydroxybutanesulfonic acids, characterized in that dithio derivatives of the general formula RH or RR, wherein R is a radical of the general formula IIa or IIb, are treated in the presence of a base with 1,4-butanesulfone or formaldehyde. in aqueous and / or aliphatic alcohol having carbon numbers. 1 to 6 at 10 to 120 ° C for 0.05 to 5 hours.