Hydrochloric Acid → Ethyl 3-chlorobenzimidate hydrochloride

HRID 1859638Notes

Reaction equation

HRID 1859638 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH2:11]([OH:13])[CH3:12]>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6](=[NH:7])[O:13][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13015Benzonitrile, m-chloro-

Product 1

HCID 21938143Ethyl 3-chlorobenzimidate hydrochlorideYield 94%

Procedure

Hydrogen chloride was bubbled through a solution of 3-chlorobenzonitrile (25.5 g, 0.185 mol) in ethanol (250 mL) to saturation under ice-cooling and the reaction mixture was stirred at room temperature for 17 hours. The solvent was distilled off under reduced pressure and the residual solid was suspended in diethyl ether (200 mL), then collected by filtration, washed with diethyl ether (200 mL) and dried in vacuo at 60° C. to give 38.3 g (94%) of ethyl 3-chlorobenzimidate hydrochloride as white crystals.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off under reduced pressure
  3. filtrationcollected by filtration
  4. washwashed with diethyl ether (200 mL)
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ed85cc2707ca4889b7a5cad0348beb5a
Source dataset
uspto-grants-2003_03
Patent number
US06528514B1

Reaction notes

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