Bromine → 7-Chloro-4-methoxy-1,3-benzothiazol-2-amine

HRID 970716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970716
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[NH:10][C:11]([NH2:13])=[S:12].BrBr>C(Cl)(Cl)Cl>[NH2:13][C:11]1[S:12][C:5]2[C:6]([Cl:9])=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[N:10]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 2732660N-(5-Chloro-2-methoxyphenyl)thiourea

Produkt 1

HCID 136667137-Chloro-4-methoxy-1,3-benzothiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 1-(2-methoxy-5-chlorophenyl)-2-thiourea (1 mmole) in chloroform (10 mL) was cooled to 10° C. and treated with bromine (2.2 mmole) in chloroform (10 mL). The reaction was stirred at 10° C. for 20 min and at room temperature for 0.5 h. The resulting suspension was heated at reflux for 0.5 h. The precipitate was collected via filtration (washed with CH2Cl2) to give 2-amino-4-methoxy-7-chlorobenzothiazole which was subjected to Steps A, B, C and D of Example 34 to give 2-amino-4-phosphonomethoxy-6-bromo-7-chloro benzothiazole (35.1). mp>220° C.(dec.). Anal. Calcd. for C8H7N2O4PSClBr: C, 25.72; H, 1.89; N, 7.50. Found: C, 25.66; H, 1.67; N, 7.23.

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 0.5 h
  3. filtrationThe precipitate was collected via filtration (washed with CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0323c84f00d640cf86c9378fc79472a5
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312219B2

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