Formamidine acetate → HCID 178420872, compound

HRID 926268Notes

Reaction equation

HRID 926268 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:8][CH2:7][CH2:6]1)=O.C(O)(=O)C.[CH:13]([NH2:15])=[NH:14]>C(O)CO.O>[CH:5]1([C:3]2[N:14]=[CH:13][NH:15][CH:2]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 110629402-Bromo-1-cyclobutylethan-1-one

Product 1

HCID 178420872HCID 178420872, compoundYield 18.6%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-bromo-1-cyclobutylethanone (27.2 g, 154 mmol) and formamidine acetate (80.0 g, 768 mmol) in ethyleneglycol (150 mL) was heated to 135° C. for 18 h. The mixture was then diluted with H2O and then continuously extracted with Et2O for 18 h. The org. phase was then dried over Na2SO4, filtered and concentrated in vacuo. Purification by distillation in a Kugelrohr oven and flash chromatography (SiO2, DCM to DCM/MeOH 9:1) afforded the title compound (3.5 g). UPLC-MS: MS 123.1 (M+H+); UPLC rt 0.36 min.

Workup

  1. extractioncontinuously extracted with Et2O for 18 h
  2. dry with materialphase was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. distillationby distillation in a Kugelrohr oven and flash chromatography (SiO2, DCM to DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-82dd285b7bfa41d2a8526825813d6704
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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