Ethanol → HCID 89854454, compound

HRID 931077Notes

Reaction equation

HRID 931077 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2([C:9]#[N:10])[CH2:8][CH2:7]2)=[N:2]1.[CH2:11]([OH:13])[CH3:12].C([Cl:17])(=O)C>>[ClH:17].[O:1]1[CH:5]=[CH:4][C:3]([C:6]2([C:9](=[NH:10])[O:13][CH2:11][CH3:12])[CH2:8][CH2:7]2)=[N:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 89853727HCID 89853727, compound

Product 1

HCID 89854454HCID 89854454, compoundYield 66.9%

Procedure

Into an 8 mL vial containing 1-(isoxazol-3-yl)cyclopropanecarbonitrile (243 mg, 1.4 mmol) and ethanol (1.98 mL, 34 mmol) was added acetyl chloride (1.45 mL, 20.4 mmol) at 0° C. The reaction mixture was stirred for 18 h at room temperature. An aliquot was removed and the solvent evaporated; 1H NMR showed the presence of product. 1H NMR (500 MHz, CDCl3) δ 1.44 (t, 3H), 1.74-1.79 (m, 2H), 2.16-2.20 (m, 2H), 4.77 (q, 2H), 6.35 (d, 1H), 8.46 (d, 1H). The reaction mixture was concentrated under reduced pressure to afford the title compound (203 mg). The material was used without further purification.

Workup

  1. customAn aliquot was removed
  2. customthe solvent evaporated
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7325cc65445496c8c2c4bfabc64dae6
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…