Sodium Carbonate → Methyl benzimidate

HRID 1179194Notes

Reaction equation

HRID 1179194 reaction equation
Cl.[CH3:2][O:3][C:4](=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[CH3:2][O:3][C:4](=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 5743287Methyl benzimidate hydrochloride

Product 1

HCID 345018Methyl benzimidateYield 81.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzimidic acid methyl ester hydrochloride (5 g, 29.1 mmol) was partitioned between saturated sodium carbonate solution (200 mL) and diethyl ether (100 mL). The organic layer was dried (MgSO4) and concentrated to provide the desired product as a colorless liquid (3.20 g, 81%). This material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 3H), 7.39-7.46 (m, 3H), 7.75 (d, J=1.1 Hz, 2H).

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f39238c15d5c4defba734efe8b8b5f9b
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

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