2-Methoxyethylamine → HCID 178495985, compound

HRID 69812Notes

Reaction equation

HRID 69812 reaction equation
[NH2:1][C:2]1[C:3]([C:7](Cl)=[N:8][OH:9])=[N:4][O:5][N:6]=1.[CH3:11][O:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C>C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:7](=[N:8][OH:9])[NH:15][CH2:14][CH2:13][O:12][CH3:11])=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 80182-Methoxyethylamine2×HCID 8471TriethylamineHCID 4040027(Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chloride

Product 1

HCID 178495985HCID 178495985, compoundYield 119%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (can be prepared according to Example 1, steps A-B, 200.0 g, 1.23 mol) was mixed with ethyl acetate (1.2 L). At 0-5° C. 2-methoxyethylamine [Aldrich, product #143693] (119.0 mL, 1.35 mol) was added in one portion while stirring. The reaction temperature rose to 41° C. The reaction was cooled to 0-5° C. Triethylamine (258 mL, 1.84 mol) was added. After stirring 5 min, LCMS indicated reaction completion. The reaction solution was washed with water (500 mL) and brine (500 mL), dried over sodium sulfate, and concentrated to give the desired product (294 g, 119%) as a crude dark oil. LCMS for C6H12N5O3 (M+H)+: m/z=202.3. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1 H), 6.27 (s, 2 H), 6.10 (t, J=6.5 Hz, 1 H), 3.50 (m, 2 H), 3.35 (d, J=5.8 Hz, 2 H), 3.08 (s, 3 H).

Workup

  1. customAt 0-5° C
  2. customrose to 41° C
  3. stirringAfter stirring 5 min
  4. customreaction completion
  5. washThe reaction solution was washed with water (500 mL) and brine (500 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae13d21c442e42d3994406751670920b
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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