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

HRID 2270993

Reaktionsgleichung

Reaktionsgleichung von HRID 2270993
[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) 1max 233 nm (sh) (e=0.589×104); (pH 6.9) 238 (sh) (0.111×104); (pH 13) 240 (sh) (0.073×104); 1H NMR d 5.25 (s, 2 H, ArCH2), 6.63 (s, 4 H, NH2, exchange with D2O), 7.30-7.42 (m, 5 H, 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-ffa74face3fb4b179c7f21ed2a191d84
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333331B1

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