Diethyl Ether → HCID 178512298, compound

HRID 1383464Notes

Reaction equation

HRID 1383464 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].CS[C:10](=[N:14][C:15]1C=CC=CN=1)[NH:11][C:12]#[N:13].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.CCOCC>N1C=CC=CC=1>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:10]([NH:11][C:12]#[N:13])=[N:14][C:15]1[CH:25]=[CH:24][N:23]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 13578DiglycolamineHCID 2761294HCID 2761294, compound

Product 1

HCID 178512298HCID 178512298, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

To a reaction flask, 2-(2-aminoethoxy)ethanol (5.78 g, 55 mmol) and S-methyl-N-cyano-N′-pyridylisothiourea (9.60 g, 50 mmol) were suspended in pyridine (40 mL). Triethylamine (7 mL, 50 mmol) was added followed by (4-dimethylamino)pyridine (cat., 100 mg). The reaction mixture became clear solution, which was stirred at 50-60° C. for 10 hours. The reaction mixture was then cooled to room temperature. Ether (200 mL) was added and the resulting solid was collected to give N-[2-(2-hydroxyethoxy)-ethyl]-N′-cyano-N″-pyridin-4-yl-guanidine (12.0 g, 48 mmol, 96%) as a white solid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe resulting solid was collected

Sources & evidence

ORD record
ord-8d76ee55359f4c6abf55f06c5a3911f4
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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