Hydrochloric Acid → 2-(4-Trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride

HRID 1433194Notes

Reaction equation

[ClH:1].[F:2][C:3]([F:15])([F:14])[C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][C:10]#[N:11])=[CH:6][CH:5]=1.[CH2:16]([OH:18])[CH3:17]>C(OCC)C>[ClH:1].[CH2:16]([O:18][C:10](=[NH:11])[CH2:9][O:8][C:7]1[CH:12]=[CH:13][C:4]([C:3]([F:14])([F:15])[F:2])=[CH:5][CH:6]=1)[CH3:17]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2M HCl in ethyl ether (92 mL) was added dropwise a solution of (4-trifluoromethyl-phenoxy)-acetonitrile (29.8 g, 0.148 mol) in ethanol (9.5 mL, 0.163 mol) at 0° C. The reaction mixture was warmed to 25° C. and stirred for 12 hours. Ethyl ether was added to precipitate the product, which was filtered and washed with ethyl ether. The collected white solid was air-dried to provide 2-(4-trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride (35.07 g, 83%) as a white solid. 1H NMR (400 MHz, CD3Cl) δ (ppm): 7.60 (d, 2H, J=8.8 Hz), 7.18 (d, 2H, J=8.4 Hz), 5.01 (s, 2H), 4.87 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.0 Hz).

Workup

customto precipitate the product, which
filtrationwas filtered
washwashed with ethyl ether
customThe collected white solid was air-dried

Sources & evidence

ORD record: ord-2819c00e59254a019a73704376fff603
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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