Tetrafluoro-m-phenylenediamine dihydrochloride → 2,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furan

Participants

Role	Name	HCID	Charge
Reactant	Tetrafluoro-m-phenylenediamine dihydrochloride	HCID 149026	—
Reactant	2,5-Bis(4-amino-3-methoxyphenyl)furan	HCID 20637356	—
Solvent	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Product	2,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furan	HCID 20637341	70%

Reaction Steps

2,5-Bis[3-methoxy-4-(2-pyridylimino)aminophenyl]furan (4o, DB746) was prepared according to the procedure for 4f using diamine 3i and S-(2-naphthylmethyl)-2-pyridylthioimidate hydrobromide as starting materials. Free base: yellow crystalline solid, mp 212-213° C. (DMF/H2O). Yield: 70%. 1H NMR (DMSO-d6): 3.82 (s, 6H), 6.89 (d, 2H), 6.98 (s, 2H), 7.38 (m, 4H), 7.54 (dd, 2H), 7.95 (dd, 2H), 8.32 (d, 2H), 8.62 (d, 2H). Dihydrochloride: yellow solid. 1H NMR (DMSO-d6): 3.97 (s, 6H), 7.36 (s, 2H), 7.47 (d, 2H), 7.62 (d, 4H), 7.85 (dd, 2H), 8.20 (d, 2H), 8.45 (d, 2H), 8.89 (d, 2H), 9.37 (br s, 2H), 10.10 (br s, 2H), 11.86 (br s, 2H). Anal. Calcd. for C30H26N6O.2.0HCl.1.0H2O (609.5): C, H, N, Cl.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06706754B2
Source dataset	uspto-grants-2004_03
ORD ID	ord-567aa75c534e4d85afcdf3df29ba4fc5
Source note	uspto-grants-2004_03