Diisopropylethylamine → HCID 178509206, compound

HRID 889400Notes

Reaction equation

[C:1]([NH:4][NH2:5])(N)=[NH:2].Cl.[CH:7]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([N:20]=[C:21]=[S:22])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:2][C:1]1[N:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([CH:7]3[CH2:9][CH2:8]3)=[CH:11][CH:12]=2)[C:21]([SH:22])=[N:5][N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), 1-cyclopropyl-4-isothiocyanato-naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50° C. for 15 hours. The solvent was evaporated, toluene was added, and the solvent was evaporated again. A 2.0 M aqueous solution of sodium hydroxide (30 mL) was added and the reaction mixture was heated at 50° C. for 60 hours. The reaction mixture was filtered, and the filtrate was neutralized with a 2.0 M aqueous solution of HCl. New filtration, then evaporation of solvent and purification of the residue by silica gel chromatography to yield 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazole-3-thiol (2.0 g, 49%).

Workup

customThe solvent was evaporated
additiontoluene was added
customthe solvent was evaporated again
additionA 2.0 M aqueous solution of sodium hydroxide (30 mL) was added
temperaturethe reaction mixture was heated at 50° C. for 60 hours
filtrationThe reaction mixture was filtered
filtrationNew filtration
customevaporation of solvent and purification of the residue by silica gel chromatography

Sources & evidence

ORD record: ord-f65086a322904e2a80a94ba227729799
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252828B2

Reaction notes

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