Potassium Carbonate → HCID 86609753, compound

HRID 1710820Notes

Reaction equation

HRID 1710820 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([Cl:24])=[C:18]([CH3:25])[C:17]=1[Br:26])C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([Cl:24])=[C:18]([CH3:25])[C:17]=1[Br:26])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86609754HCID 86609754, compound

Product 1

HCID 86609753HCID 86609753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N,N-di(tert-butyloxycarbonyl)-2-bromo-4-chloro-6-methoxy-3-methyl-phenylamine (4.1 g, 9.1 mmol) in methanol (90 ml) was heated to reflux with potassium carbonate (3.77 g, 27 mmol) for 2 days. The reaction was filtered, washed with methanol, and the solvent of the filtrate was evaporated. The residue was dissolved in diethyl ether, washed with cold 1N aqueous hydrogen chloride solution and with saturated sodium chloride solution, dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was stirred for 15 minutes with heptane. The product (2.6 g, 82%) precipitated as an off-white solid and isolated by filtration.

Workup

  1. temperaturewas heated
  2. filtrationThe reaction was filtered
  3. washwashed with methanol
  4. customthe solvent of the filtrate was evaporated
  5. dissolutionThe residue was dissolved in diethyl ether
  6. washwashed with cold 1N aqueous hydrogen chloride solution and with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe product (2.6 g, 82%) precipitated as an off-white solid
  11. customisolated by filtration

Sources & evidence

ORD record
ord-bda2a89a2a0243f9a20fddf070dc38f6
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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