Sodium Carbonate → 3-(1,3-Dioxolan-2-yl)thiophene-2-amidoxime

HRID 8709Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]#[N:12].Cl.[NH2:14][OH:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11](=[N:14][OH:15])[NH2:12]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of the foregoing nitrile (5.0 g, 27.59 mmol) in ethanol (20 ml) was added a solution of hydroxylamine hydrochloride (3.7 equivalents) and sodium carbonate (1.7 equivalents) in water (50 ml). The resulting mixture was heated to 40° C. for 5 h, then cooled to room temperature. The colourless precipitate was isolated by filtration, dried under a stream of air and azeotroped with toluene (2×) to give 3-(1,3-dioxolan-2-yl)thiophene-2-amidoxime as an off-white solid (4.36 g). 1H NMR (DMSO-d6): δ 9.83 (1H, s), 7.48 (1H, d, J 5.18), 7.15 (1H, d, J 5.18), 6.05 (1H, s), 5.77 (2H, bs), 4.05 (2H, m), 3.91 (2H, m).

Workup

temperaturecooled to room temperature
customThe colourless precipitate was isolated by filtration
customdried under a stream of air
customazeotroped with toluene (2×)

Sources & evidence

ORD record: ord-b618b7543ade454d9f721a3b5599266c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091209B2

Reaction notes

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