Hydrochloric Acid → HCID 13780008, compound

HRID 718144Notes

Reaction equation

HRID 718144 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[ClH:11].[CH2:12]([OH:14])[CH3:13]>>[ClH:11].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[NH:10])[O:14][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 13780008HCID 13780008, compoundYield 100%

Procedure

2-(4-Fluorophenyl)acetonitrile (1.0 g, 7.4 mmol) was dissolved in anhydrous ethanol (2 mL) under an atmosphere of Ar. The solution was cooled to 0° C., saturated with HCl gas, stirred for 6 h, allowed to warm to RT, and stirred for 6 h. Organic solvent was removed in vacuo to afford ethyl 2-(4-fluorophenyl)acetimidate hydrochloride (1.6 g, 100%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.27 (m, 1H), 11.20 (m, 1H), 7.40 (dd, J=8.3, 5.5 Hz, 2H), 7.19 (t, J=8.8 Hz, 2H), 4.38 (q, J=7.0 Hz, 2H), 3.99 (s, 2H), 1.25 (t, J=7.0 Hz, 3H).

Workup

  1. stirringstirred for 6 h
  2. customOrganic solvent was removed in vacuo

Sources & evidence

ORD record
ord-4468421b0ac2453e87c2e2d88ac95a43
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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