Benzyl Alcohol → 2,4-Diamino-6-benzyloxy-s-triazine

HRID 260053

Reaktionsgleichung

Reaktionsgleichung von HRID 260053
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4](Cl)[N:3]=1.[Na].[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Komponenten

4

Edukt 3

HCID 244Benzyl AlcoholHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-HCID 5360545Sodium

Produkt 1

HCID 351192,4-Diamino-6-benzyloxy-s-triazine

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2,4-Diamino-6-chloro-s-triazine (2.25 g, 15.0 mmol) was added to a solution of sodium (0.43 g, 18.8 mmol) in benzyl alcohol (30 mL) under argon. The suspension was heated in a 130° C. oil bath for 3.5 h. The excess benzyl alcohol was removed under vacuum and the resulting solid was collected with the aid of benzene, and washed with water (100 mL): yield, 1.83 g (56%); mp 184°-185° C. (lit. 186°-188° C.; Wakabayashi et al., Nippon Dojo-Hiryogaku Zasshi, 41, 193-200 (1970)); UV (pH 1) λmax 233 nm (sh) (ε=0.589×104); (pH 6.9) 238 (sh) (0.111×104); (pH 13) 240 (sh) (0.073×104); 1H NMR δ5.25 (s, 2H, ArCH2), 6.63 (s, 4H, NH2 , exchange with D2O), 7.30-7.42 (m, 5H, ArH); MS (EI) calcd. m/z for C10H11N5O 217.0963, found 217.0955.

Aufarbeitung

  1. customThe excess benzyl alcohol was removed under vacuum
  2. customthe resulting solid was collected with the aid of benzene
  3. washwashed with water (100 mL)
  4. customyield
  5. custommp 184°-185° C. (lit. 186°-188° C.; Wakabayashi et al., Nippon Dojo-Hiryogaku Zasshi, 41, 193-200 (1970))

Quellen und Nachweise

ORD-Eintrag
ord-ea57072ad3954a2c9ebf159d151f9e64
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525606

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