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

HRID 2304475Notes

Reaction equation

[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

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-

HCID 5360545Sodium

Product 1

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

Conditions

Temperature: 130 °C

Procedure

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)i (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.

Workup

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

Sources & evidence

ORD record: ord-976ffc2f42f54ce4af37fa7066181bf6
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436945B2

Reaction notes

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