2-Thenoylacetonitrile → 3-(2-Thienyl)-5-isoxazolamine

HRID 595043

Reaction equation

HRID 595043 reaction equation
[C:1]1([C:6]([CH2:8][C:9]#[N:10])=O)[S:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+]>C(Cl)Cl.CO>[S:5]1[CH:4]=[CH:3][CH:2]=[C:1]1[C:6]1[CH:8]=[C:9]([NH2:10])[O:13][N:12]=1

Participants

6

Reactant 3

HCID 1418532-ThenoylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 2169013-(2-Thienyl)-5-isoxazolamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-thenoylacetonitrile (1 g, 6.6 mmol), hydroxylamine hydrochloride (1.38 g, 19.8 mmol) and sodium acetate (2.17 g, 26.5 mmol) in DCM (20 ml) and MeOH (20 ml) was heated at 40° C. overnight, cooled to rt and concentrated. The residue was partitioned between EtOAc and water, the organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a brown solid 1-4. 1H NMR (400 MHz, CDCl3) δ 7.38 (m, 2H), 7.08 (m, 1H), 5.40 (s, 1H), 4.49 (bs, 21-1); ESI+ MS [M+H]+ C7H7N2OS=167.1.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ea3c3eee1d74e1a8557b8d98a565e31
Source dataset
uspto-grants-2016_01
Patent number
US09242995B2

Linked notes

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