Potassium Carbonate → HCID 9949549, compound

HRID 2288928Notes

Reaction equation

HRID 2288928 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[S:9]([CH2:12][C:13](OC)=[O:14])(=[O:11])=[O:10].Cl.[NH2:31][OH:32]>CO>[OH:32][NH:31][C:13](=[O:14])[CH2:12][S:9]([N:8]([CH3:7])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 131721881HCID 131721881, compound

Product 1

HCID 9949549HCID 9949549, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (124 mg, 0.9 mmol) was added to a mixture of methyl 2-({methyl[(biphen-4-yl)methyl]amino}sulfonyl)acetate (100 mg, 0.3 mmol) and hydroxylamine hydrochloride (63 mg, 0.9 mmol) in methanol (3 ml). The mixture was heated to reflux for 18 hours. The mixture was cooled and partitioned between ethyl acetate and 0.1 M aqueous hydrochloric acid. The layers were separated, and the organic layer was dried (MgSO4), and the solvents were removed under reduced pressure. The residue was triturated with diisopropyl ether to give the titled compound as a colourless solid (88 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. custompartitioned between ethyl acetate and 0.1 M aqueous hydrochloric acid
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (MgSO4)
  7. customthe solvents were removed under reduced pressure
  8. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-1476991826614c31838f2fc4245897b7
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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