Sodium Chloride → 2,7-dichloro-4-methyl-1,3-benzothiazole

HRID 1865490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865490
N[C:2]1[S:3][C:4]2[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH3:12])[C:5]=2[N:6]=1.N([O-])=O.[Na+].[Na+].[Cl-:18]>OP(O)(O)=O.O>[Cl:18][C:2]1[S:3][C:4]2[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH3:12])[C:5]=2[N:6]=1

Komponenten

6

Edukt 3

HCID 5234Sodium ChlorideHCID 20498937-Chloro-4-methyl-1,3-benzothiazol-2-amineHCID 23668193Sodium Nitrite

Produkt 1

HCID 20498762,7-dichloro-4-methyl-1,3-benzothiazoleAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1004Phosphoric AcidLösungsmittel

Versuchsvorschrift

To a slurry of 2-amino-4-methyl-7-chlorobenzothiazole (77.2) (6.37 g) in H3PO4 (85%, 213 ml) in a 500 ml 3-necked flask with mechanical stirring and an internal temperature of <−10° C., was added dropwise a solution of NaNO2 (6.87 g) in water (11 ml). The mixture was warmed to 0° for 30 minutes and then recooled. The slurry was then slowly added to a cold (˜−5° C.) solution of CuSO4.5H2O (32 g) and NaCl (40 g) in water (128 ml) with vigorous mechanical stirring. After the foaming subsides and warming to RT, the solids were collected by filtration and rinsed with water. The solids were dissolved in ether leaving some insoluble residue. The ether solution was washed with water, and sodium bicarbonate solution. After the organic layer was concentrated, the residue was purified by flash chromatography with 10% methylene chloride in hexane to afford 2-chloro-4-methyl-7-chlorobenzothiazole (77.3) (4.48 g).

Aufarbeitung

  1. temperatureThe mixture was warmed to 0° for 30 minutes
  2. filtrationthe solids were collected by filtration
  3. washrinsed with water
  4. dissolutionThe solids were dissolved in ether leaving some insoluble residue
  5. washThe ether solution was washed with water, and sodium bicarbonate solution
  6. concentrationAfter the organic layer was concentrated
  7. customthe residue was purified by flash chromatography with 10% methylene chloride in hexane

Quellen und Nachweise

ORD-Eintrag
ord-3bfe21375e0746d08f5038aa9dced3bc
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626033B2

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