Hydrochloric Acid → HCID 178428570, compound

HRID 49537Notes

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[CH3:20])=[CH:11][CH:12]=2)=[C:4]([CH3:21])[CH:3]=1.Br.C1C2C(=CC=CC=2)C=CC=1CS[C:35](=[NH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl>>[C:35]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[O:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:35](=[NH:42])[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[CH:3][C:4]=3[CH3:21])=[CH:12][CH:11]=2)=[C:14]([CH3:20])[CH:15]=1)(=[NH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 106363232,5-Bis(4-amino-2-methylphenyl)furan

HCID 68615194S-(2-naphthylmethyl)-thiobezimidate hydrobromide

Product 1

HCID 178428570HCID 178428570, compoundYield 60%

Procedure

2,5-Bis[4-(benzimidoyl)amino-2-methylphenyl]furan (4e, DB626) was prepared according to the procedure for 4f using diamine 3b and S-(2-naphthylmethyl)-thiobezimidate hydrobromide as starting materials. Free base: yellow crystalline solid. Yield: 60%. 1H NMR (DMSO-d6): 2.48 (s, 6H), 6.50 (br s, 4NH), 6.75 (s, 2H), 6.84 (s, 4H), 7.44 (m, 6H), 7.71 (d, 2H), 7.95 (d, 4H). Hydrochloride: orange/yellow hygroscopic solid. 1H NMR (DMSO-d6): 2.61 (s, 6H), 7.03 (s, 2H), 7.38-7.44 (m, 4H), 7.63-7.68 (m, 4H), 7.75-7.80 (m, 2H), 7.94 (d, 6H). MS (EI): m/z 484 (M+, 100), 3.81 (87.2), 278 (37.9), 235 (5.4), 218 (3.1), 190 (5.5), 144 (11.1), 103 (32.8), 76 (9.3). Anal. Calcd. for C32H28N4O.2HCl.0.66H2O (569.39): C, H, N.

Sources & evidence

ORD record: ord-aefef86bb17241878ddf6ec9c24a18b1
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706754B2

Reaction notes

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