Ammonium Chloride → HCID 18696600, compound

HRID 1870543Notes

Reaction equation

HRID 1870543 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:9]([C:10]2[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][O:13][CH:14]=2)[C:8](=[O:19])[N:7]([CH3:20])[N:6]=1.[NH4+].[Cl-]>CO.C(COC)OC>[CH3:1][O:2][C:5]1[N:9]([C:10]2[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][O:13][CH:14]=2)[C:8](=[O:19])[N:7]([CH3:20])[N:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 18696594HCID 18696594, compound

Product 1

HCID 18696600HCID 18696600, compound

Reagents, catalysts & solvents 1

HCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of sodium methoxide (11.4 mL, 30% in methanol) was added to a solution of the title compound of Step D (5.34 g) in methanol/dimethoxyethane (26 mL/26 mL) while stirring under nitrogen. The yellow solution was heated to 40° C. for 5 h, cooled to room temperature and left to stir overnight under nitrogen. The reaction mixture was poured into saturated aqueous NH4Cl (50 mL) and the resulting mixture was extracted three times with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated to a yellow solid. The yellow solid was dried under vacuum to afford 4.7 g of the title compound of Step E melting at 131-133° C. 1H NMR (CDCl3): δ 8.04 (d,1H), 7.68 (d,1H), 3.94 (s,3H), 3.78 (s,3H), 3.43 (s,3H).

Workup

  1. temperaturecooled to room temperature
  2. waitleft
  3. stirringto stir overnight under nitrogen
  4. extractionthe resulting mixture was extracted three times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow solid
  8. customThe yellow solid was dried under vacuum

Sources & evidence

ORD record
ord-b3e5c4cc8d3d4683b76001aa2d5308be
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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