Hydrochloric Acid → 4-Fluorobenzimidic acid ethyl ester hydrochloride

HRID 1656517Notes

Reaction equation

HRID 1656517 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[ClH:10].[O:11]1CC[CH2:13][CH2:12]1>C(O)C>[ClH:10].[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[NH:7])[O:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 145174-Fluorobenzonitrile

Product 1

HCID 122821594-Fluorobenzimidic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-fluorobenzonitrile (50 g) in tetrahydrofuran (300 mL) and ethanol (60.5 mL) at 0° C. was saturated with anhydrous hydrogen chloride gas and the resulting solution was allowed to stand overnight. The solvent was evaporated and the resulting solid was collected and washed with ether to provide ethyl 4-fluorobenzimidate hydrochloride as a white solid (20 g); NMR: 8.27 (m,2), 7.51 (m,2), 4.63 (q,2), 1.47 (t,3).

Workup

  1. customat 0° C.
  2. customThe solvent was evaporated
  3. customthe resulting solid was collected
  4. washwashed with ether

Sources & evidence

ORD record
ord-c1a6320558b6436bb8ca96d5073c58a1
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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