Ammonium Chloride → HCID 91536585, compound

HRID 527948Notes

Reaction equation

HRID 527948 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[C:6]([CH:13]3[CH2:15][O:14]3)[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[NH4+].[Cl-].[N-:18]=[N+:19]=[N-:20].[Na+]>CO>[N:18]([CH:13]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[N:11]2)[CH2:15][OH:14])=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 85911716HCID 85911716, compound

Product 1

HCID 91536585HCID 91536585, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-methoxy-8-oxiranyl-quinoxaline (4.7 g, 23 mmol; prepared as in WO 2004/002490), NH4Cl (2.2 g, 1.8 eq.) and NaN3 (3.8 g, 2.5 eq.) in MeOH (60 mL) was heated at 65° C. for 5 h, filtered and concentrated in vacuo. The residue was taken up in EA and washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 1:1) to give the desired intermediate as a beige solid (4.4 g, 77% yield).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by CC (Hept/EA 1:1)

Sources & evidence

ORD record
ord-9635b01719c449b6bc131b5b34cb3227
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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