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Cyanamide → 2-(4-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate

HRID 705917
Notes
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Reaction equation

HRID 705917 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N:22]#[C:23][NH2:24].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:23](=[NH:22])([O:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:4]2[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:14][CH:15]=1)[NH2:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677727742-(4-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}phenyl)ethanol

Product 1

HCID 677757672-(4-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamateYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-{[3-chloro-5-(trifluoromethyl)phenyl]oxy}phenyl)ethanol (2 g, 6.32 mmol) and cyanamide (0.4 g, 9.51 mmol) in dry THF (20 mL) under nitrogen was added triflic acid (0.8 mL, 9.01 mmol). The mixture was heated at 55° C. for 4 h. Purification via reverse phase flash chromatography afforded the title compound (2.1 g, 4.45 mmol, 70.5% yield) as a brown oil. LCMS: rt=2.95 min, [M+H+]=359

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-cbaf9b859bf2408583c8c316b0156ed4
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes