Diisopropylethylamine → HCID 178509206, compound

HRID 660454Notes

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-isothiocyanatonaphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50° C. for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50° C. for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol (2.0 g, 49%).

Workup

customThe solvent was removed under reduced pressure, toluene
additionadded
customthe solvent was evaporated again
additionSodium hydroxide solution (2M, 30 mL) was added
temperaturethe reaction mixture heated at 50° C. for 60 hours
filtrationThe reaction mixture was filtered
filtrationThe mixture was re-filtered
customthe solvent removed under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-18465e526b9a4c818606dfc57098dd47
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084483B2

Reaction notes

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