Ammonia → 1-(Adamantan-1-yl)thiourea

Reaction equation

[C:1]12([N:11]=[C:12]=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH3:14]>>[C:1]12([NH:11][C:12]([NH2:14])=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Reactant 2

HCID 222Ammonia

HCID 107279Adamantyl isothiocyanate

Product 1

HCID 7964291-(Adamantan-1-yl)thiourea

Procedure

A mixture of 1-adamantyl isothiocyanate (4.83 g, 25.0 mmol, Aldrich) and ammonia (0.5 M solution in 1,4-dioxane, 100 mL, 50 mmol) was stirred at ambient temperature for 48 h. The solvents were removed in vacuo to give the title compound as a white solid. MS m/z: 211.1 (M+H)+.

Workup

customThe solvents were removed in vacuo

Sources & evidence

ORD record: ord-288db09c604c42359a5d1e34100371d1
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253196B2

Reaction notes

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