Cyanamide → 2-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamate

HRID 474669Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[N:19]#[C:20][NH2:21].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:20](=[NH:19])([O:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=2)=[CH:11][CH:12]=1)[NH2:21]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-{4-[(3-fluoro-4-methylphenyl)oxy]phenyl}ethanol (1 g, 4.06 mmol) and cyanamide (0.205 g, 4.87 mmol) in dry THF (15 mL) under nitrogen was added triflic acid (0.433 mL, 4.87 mmol). The mixture was heated at 55° C. for 2 h. Purification via reverse phase flash chromatography afforded the title compound (420 mg, 1.047 mmol, 25.8% yield) as white solid. LCMS: rt=2.61 min, [M+H+]=229

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-b8f1e49e335c4422a50fe5fe2bd7714e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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