Hydroxyamine hydrochloride → 5,6,7,8-Tetrahydro-1H-benzo[b]cyclopenta[d]thiophen-3(2H)-one Oxime

HRID 592535Notes

Reaction equation

Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH2:9]1[C:13]2[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[S:16][C:12]=2[C:11](=O)[CH2:10]1>CO>[CH2:9]1[C:13]2[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[S:16][C:12]=2[C:11](=[N:2][OH:3])[CH2:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a mechanical stirrer and nitrogen inlet was charged with hydroxylamine hydrochloride (573 mg, 8.25 mmol) and methanol (10 mL). The mixture was cooled to 0° C. using an ice bath. Sodium acetate (677 mg, 8.25 mmol) was added. The mixture was stirred at 0° C. for 30 min. After this time, 105c (319 mg, 1.65 mmol) was added, and the reaction was stirred at room temperature for 16 h. After this time, the mixture was concentrated, and the resulting residue was triturated with water (10 mL). The resulting solid was collected and dried in a vacuum oven at 45° C. to afford an 84% yield (287 mg) of 105d as an off-white solid: mp 173-174° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.38 (s, 1H), 2.97 (m, 2H), 2.77-2.73 (m, 4H), 2.47 (m, 2H), 1.75 (m, 4H); MS (APCI+) m/z 208.3 (M+H)

Workup

customA 100-mL single-neck round-bottomed flask equipped with a mechanical stirrer and nitrogen inlet
stirringthe reaction was stirred at room temperature for 16 h
concentrationAfter this time, the mixture was concentrated
customthe resulting residue was triturated with water (10 mL)
customThe resulting solid was collected
customdried in a vacuum oven at 45° C.

Sources & evidence

ORD record: ord-159a57e8208243ba82f40a59f59b8e3b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

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