Potassium Carbonate → 2-(1,1-dimethylethylsulfinamido)-N'-hydroxy-2-methylpropanimidamide

HRID 1854731Notes

Reaction equation

HRID 1854731 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])([CH3:11])[CH3:10])#[N:8].Cl.[NH2:20][OH:21]>CCO>[CH3:16][C:15]([CH3:18])([S:13]([NH:12][C:9]([CH3:11])([CH3:10])[C:7](=[N:20][OH:21])[NH2:8])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 90402306HCID 90402306, compound

Product 1

HCID 904022952-(1,1-dimethylethylsulfinamido)-N'-hydroxy-2-methylpropanimidamideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (2.94 g, 21.2 mmol) was added to a stirring solution of N-(2-cyanopropan-2-yl)-2-methylpropane-2-sulfinamide (1.0 g, 5.3 mmol) and hydroxylamine hydrochloride (738 mg, 10.6 mmol) in EtOH (18 mL) at rt. The reaction was heated to 60° C. for 16 h. The reaction was then concentrated and the resulting residue was diluted with EtOAc and washed with water, and sat NaCl aq. The organic phase was dried over Na2SO4, filtered and concentrated azeotroping with toluene to give the expected product 2-(1,1-dimethylethylsulfinamido)-N′-hydroxy-2-methylpropanimidamide (1.0 g, 4.5 mmol, 85% yield) as a white solid consistent by LCMS and NMR. LC-MS retention time: 0.35 min; m/z (MH+): 222. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (400 MHz, DMSO-d6) δ 9.14 (s, 1H), 5.27 (s, 1H), 5.25 (s, 2H), 1.36 (d, J=5.0 Hz, 6H), 1.12 (s, 9H).

Workup

  1. concentrationThe reaction was then concentrated
  2. additionthe resulting residue was diluted with EtOAc
  3. washwashed with water
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customazeotroping with toluene

Sources & evidence

ORD record
ord-865780f5f3e74a80a33476735814d739
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

Loading…