Cyanamide → 4-(4-Fluorophenoxy)phenethyl carbamimidate

HRID 474641Notes

Reaction equation

HRID 474641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[N:18]#[C:19][NH2:20].FC(F)(F)S(O)(=O)=O>C1COCC1>[C:19](=[NH:18])([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1)[NH2:20]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677754954-(4-Fluorophenoxy)phenethyl alcohol

Product 1

HCID 679525344-(4-Fluorophenoxy)phenethyl carbamimidateYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{4-[(4-fluorophenyl)oxy]phenyl}ethanol (750 mg, 3.23 mmol) and cyanamide (149 mg, 3.55 mmol) in THF (15 mL) was added trifluoromethanesulfonic acid (0.344 mL, 3.88 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via reverse phase flash chromatography then afforded the title compound (290 mg, 1.057 mmol, 32.7% yield).

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-cefec08e60fc449084868357a1528767
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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