Derivatives of xanthates and aromatic nitro and amino compounds was written by Csuros, Zoltan;Rusznak, Istvan. And the article was included in Magyar Chemiai Folyoirat in 1944.Electric Literature of C8H9NO3 This article mentions the following:
Cellulose xanthate, dry or in solution, can be stabilized by salts of aromatic nitro sulfonic acids, e.g. m-O2NC6H4SO8H (I). The structure of the products was proved by model experiments with simple xanthates which gave crystalline derivatives Alkali salts (except K) of I, m-O2NC6H4NH2, PhNO2, and m-O2NC6H4NHAc, seem to be effective as stabilizers. The products are esters of PhNHCSOH formed according to the equation 4RNO2 + 6R’OCS2Na + 3H2O = 4RNHCSOR’ (II) + 3Na2S2O3 + CO2 + CS2 + 2R’OH. The following II were prepared Thiocarbanilates, PhNHCSOR (R’ given): Me (32.5% from MeOCS2Na in 90% MeOH with PhNO2), m. 97.5° (S 18.93, N 8.27, PhNH2 46.35-7.92%); Et (27.2% from EtOCS2Na in 90% EtOH), m. 70° (S 18.1, N 7.68, PhNH2 45.55-7.00%); iso-Bu (35.7% from iso-BuOCS2Na in 90% EtOH), m. 75° (S 15.0, N 6.6%). m-Sulfothiocarbanilates: Me (67.6% from MeOCS2Na and m-O2NC6H4SO2Na (III) in MeOH), contained S 24.0, N 5.18%; Et (88.1%), m. 270-5° (S 22.10, N 4.85, PhNH2 27.2-8.9%); iso-Bu (58.8%), m. 243-5° (S 19.9, N 4.39%); glyceryl (34.5% from glycerol xanthate and III in aqueous EtOH 4 h. at 35° and 20 mm.), amorphous, m. 153-5° (S 19.31, N 4.31%). Cellulose xanthate (7%) diluted with water and treated with 5-10% AcOH, the liberated H2S removed, and the solution treated with III 10 h. as above, gives a product (S 12.02, N 2.13, PhNH2 12.3-13.9%), identical with that obtained by Lilienfeld; the same compound was obtained by treating 7% cellulose xanthate with NaOH, centrifuging, mixing with III, treating with CS2, again dissolving in NaOH, and precipitating with saturated NaCl solution Me m-acetamidothiocarbanilate, m. 168° (N 12.39, S 14.37%), was obtained in 69.3% yield from MeOCS2Na and m-O2NC6H4NHAc in 60% MeOH and AcOH heated 15 h. at 60°; Et ester (64.6%), m. 154° (N 11.61, S 13.64%). Me m-nitrothiocarbanilate (45% from MeOCS2Na and m-O2NC6H4NH2 in 60% MeOH and a bit of solid KOH heated 50 h. on a water bath), m. 119° (S 15.0, N 13.16%); Et ester, m. 115° (S 14.24, N 12.22%). The methods proposed by Orndorff and Richmond [Am. Chem. J. 22, 458(1899)] and Hofmann [Ber. 2, 120 (1889)] were also tested. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Electric Literature of C8H9NO3).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Electric Literature of C8H9NO3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem