Hydrochloric Acid → Ethyl 3-chlorobenzimidate hydrochloride

HRID 1508698Notes

Reaction equation

HRID 1508698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:10]([OH:12])[CH3:11].Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[NH:6])[O:12][CH2:10][CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

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

Product 1

HCID 21938143Ethyl 3-chlorobenzimidate hydrochlorideYield 65%

Procedure

An 100-mL round bottomed flask was charged with 3-chlorobenzonitrile (2.75 g, 20 mmol, 1 eq.), ethanol (1 g, 22 mmol, 1.1 eq.), HCl (4 N in dioxane, 20 ml, 80 mmol, 4 eq.). The resulting mixture was stirred at rt for 48 hr. The volatile material was removed under reduced pressure and the residue was treated ether. Solid was collected by filtration and washed with ether. The product thus obtained was forwarded to the next step without any further purification (2.87 g, 65% yield).

Workup

  1. customThe volatile material was removed under reduced pressure
  2. additionthe residue was treated ether
  3. filtrationSolid was collected by filtration
  4. washwashed with ether
  5. customThe product thus obtained
  6. customwas forwarded to the next step without any further purification (2.87 g, 65% yield)

Sources & evidence

ORD record
ord-f4658becdd17483897ef7f55d5cbdcc4
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…