Water → N'-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide

HRID 69813

Reaction equation

HRID 69813 reaction equation
[NH2:1][C:2]1[C:3]([C:7](=[N:13][OH:14])[NH:8]CCOC)=[N:4][O:5][N:6]=1.O.[OH-].[K+].[C:18]([O:21][CH2:22]C)(=O)[CH3:19]>CCCCCC>[OH:14][N:13]=[C:7]([C:3]1[C:2]([NH:1][CH2:19][CH2:18][O:21][CH3:22])=[N:6][O:5][N:4]=1)[NH2:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 178495985HCID 178495985, compound

Product 1

HCID 136330164N'-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamideYield 81%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Amino-N′-hydroxy-N-(2-methoxyethyl)-1,2,5-oxadiazole-3-carboximidamide (248.0 g, 1.23 mol) was mixed with water (1 L). Potassium hydroxide (210 g, 3.7 mol) was added. The reaction was refluxed at 100° C. overnight (15 hours). TLC with 50% ethyl acetate (containing 1% ammonium hydroxide) in hexane indicated reaction completed (product Rf=0.6, starting material Rf=0.5). LCMS also indicated reaction completion. The reaction was cooled to room temperature and extracted with ethyl acetate (3×1 L). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (201 g, 81%) as a crude off-white solid. LCMS for C6H12N5O3 (M+H)+: m/z=202.3 1H NMR (400 MHz, DMSO-d6): δ 10.54 (s, 1 H), 6.22 (s, 2 H), 6.15 (t, J=5.8 Hz, 1 H), 3.45 (t, J=5.3 Hz, 2 H), 3.35 (m, 2 H), 3.22 (s, 3 H).

Workup

  1. customreaction
  2. customLCMS also indicated reaction completion
  3. temperatureThe reaction was cooled to room temperature
  4. extractionextracted with ethyl acetate (3×1 L)
  5. dry with materialThe combined ethyl acetate solution was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ad5a18175e240d19a0c2bfb633c5479
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Linked notes

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