ChemicalBook CAS DataBase List N-(4-METHOXY-PHENYL)-GUANIDINE

N-(4-METHOXY-PHENYL)-GUANIDINE synthesis

7synthesis methods

Product Name:N-(4-METHOXY-PHENYL)-GUANIDINE
CAS Number:67453-80-9
Molecular formula:C8H11N3O
Molecular Weight:165.19

420-04-2 Synthesis

420-04-2
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104-94-9 Synthesis

104-94-9
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$9.00/1g

67453-80-9
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Yield:67453-80-9 80%

Reaction Conditions:

with scandium tris(trifluoromethanesulfonate) in water at 100; for 48 h;

Steps:

General Procedure for the Guanylation of Amines:

To a solution of p-methoxyaniline (1b, 61.6 mg, 0.50 μmol)and cyanamide (25.2 mg, 0.60 μmol) in H2O (2.5 mL) wasadded Sc(OTf)3 (24.6 mg, 50 nmol) at r.t. After the solutionwas stirred at 100 °C for 2 d, the resulting mixture waswashed with CHCl3 (3 × 10 mL). The aqueous layer wasconcentrated in vacuo, and the residue was purified by filtering through silica gel pad (CHCl3-MeOH, 20:1) to give2b as a purple solid (66.1 mg, 80%). IR (neat): 3353, 2158,1673, 1513, 1244, 1028 cm-1. 1H NMR (400 MHz, CD3OD,25 °C): δ = 7.10 (d, J = 9.1 Hz, 2 H), 6.91 (d, J = 9.1 Hz, 2H), 3.72 (s, 3 H). 13C NMR (100 MHz, CD3OD, 25 °C): δ =164.8, 160.9, 128.9, 128.1, 116.2, 56.0. ESI-MS: m/z calcdfor C8H11N3O [M + H]+: 166.1; found: 166.1.

References:

Tsubokura, Kazuki;Iwata, Takayuki;Taichi, Misako;Kurbangalieva, Almira;Fukase, Koichi;Nakao, Yoichi;Tanaka, Katsunori [Synlett,2014,vol. 25,# 9,p. 1302 - 1306]