Sodium Hydroxide → 6-[(2,6-Dichlorobenzyl)oxy]-1,3-benzothiazol-2-amine

HRID 1929343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929343
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[NH2:11][C:12]1[S:13][C:14]2[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=2[N:16]=1.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=1[CH2:2][O:21][C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([NH2:11])[S:13][C:14]=2[CH:20]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 334622-Amino-6-benzothiazololHCID 516892Sodium Bicarbonate

Produkt 1

HCID 866469386-[(2,6-Dichlorobenzyl)oxy]-1,3-benzothiazol-2-amineAusbeute 17,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

add 289 mg of 2-(bromomethyl)-1,3-dichlorobenzene to a solution of 200 mg of 2-amino-1,3-benzothiazol-6-ol in 12.1 cm3 of a 0.1N aqueous solution of sodium hydroxide. The suspension obtained is stirred for 24 hours at about 20° C. The pH is then adjusted to the range 4-5 by adding glacial acetic acid then to 6-7 by adding solid sodium hydrogen carbonate. The mixture obtained is extracted 3 times with 40 cm3 of dichloromethane. The organic phases are combined, dried over magnesium sulphate, treated with vegetable black, then filtered and concentrated under reduced pressure (0.2 kPa). After purification of the residue by filtration on silica [eluent: dichloromethane/methanol (95/5 by volume)], we obtain 70 mg of 6-[(2,6-dichlorobenzyl)oxy]-1,3-benzothiazol-2-amine in the form of a grey meringue, which has the following characteristics:

Aufarbeitung

  1. customThe suspension obtained
  2. customThe mixture obtained
  3. extractionis extracted 3 times with 40 cm3 of dichloromethane
  4. dry with materialdried over magnesium sulphate
  5. additiontreated with vegetable black
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (0.2 kPa)
  8. customAfter purification of the residue
  9. filtrationby filtration on silica [eluent: dichloromethane/methanol (95/5 by volume)], we

Quellen und Nachweise

ORD-Eintrag
ord-7bfe4fefda2541309870d798a8b6d24a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188078B2

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