Hydrochloric Acid → Ethyl 5-chloro-2-methoxybenzimidate hydrochloride

HRID 254678Notes

Reaction equation

HRID 254678 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:12]([OH:14])[CH3:13].Cl>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7](=[NH:8])[O:14][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 28009795-Chloro-2-methoxybenzonitrile

Product 1

HCID 66851771Ethyl 5-chloro-2-methoxybenzimidate hydrochlorideYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled solution of 5-chloro-2-methoxybenzonitrile (9.3 g, 0.056 mol, Maybridge) and ethanol (16.2 mL, 0.28 mol) in CH2Cl2 (40 mL) was bubbled with HCl gas at 0° C. for 30 min. The reaction mixture was kept in refrigerator for 5 days. The reaction mixture was then concentrated and triturated with diethyl ether to remove unreacted starting material. The precipitate was dried under reduced pressure to obtain 7.1 g (51%) of the title compound. MS (ESI+) m/z 214 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customtriturated with diethyl ether
  3. customto remove unreacted
  4. customThe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-adb3fdd9b05a44fdb12a208613f3da3c
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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