Ammonia → 3-Chloro-benzamidine

HRID 1508670Notes

Reaction equation

HRID 1508670 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6](=[NH:10])OCC.[NH3:14]>CO>[Cl:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6](=[NH:10])[NH2:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21938143Ethyl 3-chlorobenzimidate hydrochloride

Product 1

HCID 2041443-Chloro-benzamidineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1-L round bottom flask was charged with ethyl 3-chlorobenzimidate hydrochloride (26.9 g, mmol, 122 mmol, 1 eq.) and NH3 (7N in methanol, 360 mL, 2.52 mol, 20 eq.) in methanol (270 mL). The resulting mixture was stirred at room temperature for 3 days. The volatile material was removed under reduced pressure and the resultant off-white solid was used in the next step without further purification (23.9 g, 89% yield). 1H NMR (DMSO-d6, 500 MHz) δ 9.48 (br s, 4H), 7.97-7.94 (m, 1H), 7.84-7.79 (m, 2H), 7.65 (t, J=8.0 Hz, 1H).

Workup

  1. customThe volatile material was removed under reduced pressure
  2. customthe resultant off-white solid was used in the next step without further purification (23.9 g, 89% yield)

Sources & evidence

ORD record
ord-ecceb114412b4a8fa50da7d61ddb5ecb
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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