Aminoacetonitrile hydrochloride → 5-Amino-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione

HRID 863071Notes

Reaction equation

[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)=[C:2]=[S:3].Cl.[NH2:15][CH2:16][C:17]#[N:18]>C(N(CC)CC)C>[NH2:15][C:16]1[N:1]([CH:4]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)[C:2](=[S:3])[NH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-isothiocyano-1,2,3,4-tetrahydronaphthalene (1.92 g, 10.1 mol), prepared as in Example 10, and aminoacetonitrile hydrochloride (0.94 g, 10.1 mmol) in 1.41 mL of triethylamine was heated at 60° C. for 1 hour. The solvent was evaporated and the residue was purified by flash chromatography (elution: methylene chloride followed by 3% methanol in methylene chloride). The purified residue was recrystallized from ethyl acetate/hexane. The residue (1.06 g) and 44 mL of 0.1N potassium hydroxide was stirred under nitrogen for 15 minutes. The residue was isolated by filtration, washed with water, air dried and then stirred with methylene chloride. Filtration and drying gave 5-amino-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione, m.p. 169°-171° C.

Workup

customThe solvent was evaporated
customthe residue was purified by flash chromatography (elution: methylene chloride followed by 3% methanol in methylene chloride)
customThe purified residue was recrystallized from ethyl acetate/hexane
customThe residue was isolated by filtration
washwashed with water, air
customdried
stirringstirred with methylene chloride
filtrationFiltration
customdrying

Sources & evidence

ORD record: ord-723a0aba5c824f788469e0c9d093be21
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719280

Reaction notes

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