Hydrochloric Acid → Ethyl 4-methoxybenzimidate hydrochloride

HRID 732109Notes

Reaction equation

HRID 732109 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[ClH:11].[CH3:12][CH2:13][OH:14]>>[ClH:11].[CH2:13]([O:14][C:7](=[NH:8])[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 701294-Methoxybenzonitrile

Product 1

HCID 12270046Ethyl 4-methoxybenzimidate hydrochloride

Procedure

4-Methoxybenzonitrile and 24% hydrochloric acid in EtOH were mixed at 0° C. This mixture was left stirring at r.t. o.n., followed by concentration in-vacuo. The isolated residue was triturated with Et2O to isolate the title compound (1.25 g). 1H-NMR: 12.3 (br. s, 1H), 11.6 (br. s, 1H), 8.43 (d, 2H), 7.04 (d, 2H), 4.91 (t, 3H), 3.90 (s, 3H), 1.61 (t, 3H).

Workup

  1. waitThis mixture was left
  2. concentration, followed by concentration in-vacuo
  3. customThe isolated residue was triturated with Et2O

Sources & evidence

ORD record
ord-ba62451620744e60b21eb9bf45972ea4
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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