Ethanol → HCID 178515904, compound

HRID 1019644Notes

Reaction equation

HRID 1019644 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-8000029250f54c4d82e14cdfe42cd334
Source dataset
uspto-grants-2014_05
Patent number
US08716283B2

Reaction notes

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