Acetic Acid → HCID 178527790, Verbindung

HRID 1110377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110377
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[C:6]([SH:8])[CH:7]=1.[C:10](=S)=[S:11].C(O)(=O)C>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:10]([SH:11])[S:8][C:6]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 27375182-Amino-5-chlorobenzenethiol

Produkt 1

HCID 178527790HCID 178527790, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4-Chloroaniline (14.3g, .112mol) was dissolved in 30 mL of glacial acetic acid and added slowly to S2Cl2 (75 mL) cooled in a CH2OH--ice bath. The reaction was stirred for 15 hours at room temperature. It was then increased to 50° C. for 4 hours and then to 78° C. for 3 hours. The reaction was cooled and 100 mL of dry benzene added. The mixture was stirred for 30 minutes and filtered. The product was washed two times with 25 mL of benzene. The green/yellow substance was added to 250 mL of crushed ice and 150mL of H2O and stirred 3 hours. The purple product was filtered and added with vigorou stirring to cooled 5% NaOH. The reaction was stirred to one hour, filtered and the pH adjusted to 7 with dilute acetic acid. The product precipitated and was isolated by vacuum filtration to yield 10.7g of 5-chloro-2-aminobenzenethiol (59.8% yield): m.p. 70° -72° C.; NMR(DMSO-d6) δ7.3-6.7(m, 3H); 5.7-4.7(s, 3H); mass spectrum, m/e 159(M calcd. 159.6) 5-Chloro-2-aminobenzenethiol(15g, 0.095mol) was dissolved in 5% NaOH and 17mL of carbon disulfide were added. The reaction was stirred 15 hours at room temperature and heated at reflux for 3 hours. The pH of the reaction was adjusted to 6 with dilute acetic acid and filtered to yield 16.9g of 6-chloro-2-mercaptobenzothiazole (89.4% yield): m.p. 243° -246° C. (decomposes); NMR(DMSO-d6) δ11.5(s, lH); 8.0-7.2(m, 3H)

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cc6ef8e2d5ec4de2ab64dfc204928e53
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04975449

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