Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 20637335, compound

HRID 49539Notes

Reaction equation

HRID 49539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=3[Cl:20])=[CH:11][CH:12]=2)=[C:4]([Cl:21])[CH:3]=1.[C:22]1([NH2:33])[C:27](F)=[C:26](F)[C:25](F)=[C:24]([NH2:31])C=1F.Cl.Cl>CCO>[Cl:20][C:14]1[CH:15]=[C:16]([N:19]=[N:31][C:24]2[CH:25]=[CH:26][CH:27]=[CH:22][N:33]=2)[CH:17]=[CH:18][C:13]=1[C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:1]=[N:31][C:24]3[CH:25]=[CH:26][CH:27]=[CH:22][N:33]=3)=[CH:3][C:4]=2[Cl:21])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 104958462,5-Bis(4-amino-2-chlorophenyl)furan

Product 1

HCID 20637335HCID 20637335, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,5-Bis[2-chloro-4-(2-pyridylimino)aminophenyl]furan (4j, DB712) was prepared according to the procedure for 4f using diamine 3d and S-(2-naphthylmethyl)2-pyridylthioimidate hydrobromide as starting materials. Free base: orange crystalline solid, mp 189-190° C. (EtOH). Yield: 25%. 1H NMR (DMSO-d6): 6.85 (br s, 4NH), 7.02 (dd, 2H), 7.08 (d, 2H), 7.17 (s, 2H), 7.56 (m, 2H), 7.93-7.98 (m, 4H), 8.29 (d, 2H), 8.64 (m, 2H). Dihydrochloride: yellow/orange solid, mp>180° C. dec. 1H NMR (DMSO-d6): 7.45 (s, 2H), 7.60 (d, 2H), 7.80 (s, 2H), 7.86 (dd, 2H), 8.23 (m, 4H), 8.50 (d, 2H), 8.90 (d, 2H), 9.54 (br s, 2H), 10.23 (br s, 2H), 11.98 (br s, 2H). MS (EI): m/z 530, 528, 526 (M+, 13.2, 69.8, 100), 426, 424, 422 (7.9, 48, 72.4), 322, 320, 318 (2.6, 17.4, 26.6). Anal. Calcd. for C28H20Cl2N6O.2.0HCl.1.5H2O (627.35): C, H, N, Cl.

Sources & evidence

ORD record
ord-f1820e24c3b047748fef608da7592645
Source dataset
uspto-grants-2004_03
Patent number
US06706754B2

Reaction notes

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