Ethanol → HCID 178515904, compound

HRID 523871Notes

Reaction equation

HRID 523871 reaction equation
Cl.[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=[NH:11])OCC)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].C(O)C.[CH2:20](N)[CH2:21][NH2:22]>CCOCC>[CH2:20]1[NH:11][C:7](=[C:6]2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[C:3](=[O:2])[CH:13]=[CH:12]2)[NH:22][CH2:21]1

Participants

5

Reactant 3

HCID 702EthanolHCID 3301EthylenediamineHCID 136331260HCID 136331260, compound

Product 1

HCID 178515904HCID 178515904, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the imidate ester HCl 34 (650 mg, 2.63 mmol) in abs. ethanol was added ethylenediamine (0.53 ml, 7.89 mmol) at 0° C. and the mixture was stirred for 16 hrs at room temperature. Ether was added and the resulting precipitates were collected by filtration and dried in vacuo to give 490 mg (90% yield) of the desired cyclic amidine 35. 1H NMR (600 MHz, DMSO-d6) δ 8.38 (d, 1H, J=3 Hz), 7.45 (dd, 1H, J=9, 2.4 Hz), 3.79 (s, 4H).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5e928f7ed6b648afb143221f9793fb88
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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