Hydrochloric Acid → Ethyl 3-chlorobenzimidate hydrochloride

HRID 1508669Notes

Reaction equation

HRID 1508669 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]([CH:7]=[CH:8][CH:9]=1)[C:5](=[NH:6])[O:12][CH2:10][CH3:11]

Participants

4

Reactant 3

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

Product 1

HCID 21938143Ethyl 3-chlorobenzimidate hydrochlorideYield 84%

Procedure

A 500-mL round bottomed flask was charged with 3-chlorobenzonitrile (23.3 g, 169 mmol, 1 eq.), ethanol (8.48 g, 184 mmol, 1.09 eq.), and HCl (4 N in dioxane, 169 mL, 676 mmol, 4 eq.). The resulting mixture was stirred at room temperature for 54 hr. The volatile material was removed under reduced pressure and the residue was treated with ether. The resulting solid was collected by filtration and washed with ether. The product was used in the next step without further purification (26.9 g, 84% yield). 1H NMR (DMSO-d6, 500 MHz) δ 12.0 (br s, 2H), 8.25-8.20 (m, 1H), 8.12-8.08 (m, 1H), 7.90-7.85 (m, 1H), 7.67 (t, J=8.0 Hz, 1H), 4.63 (q, J=7.0 Hz, 2H), 1.48 (t, J=7.0 Hz, 3H).

Workup

  1. customThe volatile material was removed under reduced pressure
  2. additionthe residue was treated with ether
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ether
  5. customThe product was used in the next step without further purification (26.9 g, 84% yield)

Sources & evidence

ORD record
ord-54c318930cec4a0aa9995e0f0692e75d
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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