Cyanamide → HCID 67952566, compound

HRID 474695Notes

Reaction equation

HRID 474695 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([F:18])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=2)=[C:4]([F:19])[CH:3]=1.[N:20]#[C:21][NH2:22].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:21](=[NH:20])([O:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[C:16]([F:18])=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=2[F:19])=[CH:8][CH:9]=1)[NH2:22]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677756402-(4-(4-Chloro-2,6-difluorophenoxy)phenyl)ethanol

Product 1

HCID 67952566HCID 67952566, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(4-chloro-2,6-difluorophenoxy)phenyl)ethanol (1.6 g, 5.62 mmol) and cyanamide (0.600 g, 14.27 mmol) in dry THF (10 mL) under nitrogen was added triflic acid (1.3 mL, 14.64 mmol) at 0° C. The mixture was stirred at room temperature for 2 h. Purification via reverse phase flash chromatography afforded the title compound (1.74 g, 3.65 mmol, 64.9% yield). LCMS: rt=2.66 min, [M+H+]=327

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-be27c03c52fb46f5aa2b056e649491ee
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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