Bromine → 2-Amino-6-benzylbenzothiazole

HRID 9125

Reaktionsgleichung

Reaktionsgleichung von HRID 9125
[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([S-:17])#[N:16].[K+].BrBr>C(O)(=O)C>[NH2:16][C:15]1[S:17][C:13]2[CH:14]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=[CH:10][C:11]=2[N:12]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 136914Benzenamine, 4-(phenylmethyl)-HCID 516872Potassium thiocyanate

Produkt 1

HCID 219855102-Amino-6-benzylbenzothiazoleAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of 4-benzylaniline (0.916 g, 5.00 mmol) and KSCN (0.97 g, 10.0 mmol, 2.0 eq) in 10 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.258 mL, 5.00 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 1 hour. The precipitate was filtered off and washed with Et2O. The obtained solid was neutralized with saturated sodium carbonate solution, and a new precipitate was formed. It was filtered off, washed with water and MeOH, and dried under vacuum to give the desired compound 1.06 g (88%). LC/MS 241.2 (M+1); LC retention time 2.46 min.

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O
  3. customa new precipitate was formed
  4. filtrationIt was filtered off
  5. washwashed with water and MeOH
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-74007a0173b8457e84bcfc9f8de348a6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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