Sulfurous Acid → N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine

HRID 907722

Reaktionsgleichung

Reaktionsgleichung von HRID 907722
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[S:10])=[CH:4][CH:3]=1.BrBr.S(=O)(O)O.[OH-].[NH4+]>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:17]3[CH:16]=[C:15]([CH3:18])[CH:14]=[CH:13][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1100Sulfurous AcidHCID 14923Ammonium HydroxideHCID 24408BromineHCID 5017958N-(4-iodophenyl)-N'-(4-methylphenyl)thiourea

Produkt 1

HCID 21985719N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

A suspension of N-(4-iodophenyl)-N′-(4-methylphenyl) thiourea (0.62 g, 4.68 mmol) in chloroform (23 mL) was treated with a solution of bromine (2.65 g, 16.59 mmol) in chloroform (1 mL). The reaction mixture was stirred at rt for 5 minutes and then heated at 50° C. for 5 minutes. Then the reaction mixture was allowed to cool, and was treated with sulphurous acid until the orange color disappeared. The reaction mixture was neutralized by treatment with conc. ammonium hydroxide. More chloroform was then added to dissolve the precipitate. The layers was separated, and the organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to give N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine (0.6 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ 2.36 (s, 3H), 7.12 (m, 1H), 7.48 (d, 1H), 7.60 (m, 3H), 7.65 (m, 2H), 10.50 (s, 1H).

Aufarbeitung

  1. temperatureheated at 50° C. for 5 minutes
  2. temperatureto cool
  3. dissolutionto dissolve the precipitate
  4. customThe layers was separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e636b031ff34a938104351f61128891
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013166B2

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