Potassium Carbonate → HCID 22476609, compound

HRID 2184413Notes

Reaction equation

HRID 2184413 reaction equation
[OH:1][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10].Br[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][C:2]1([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:23][C:24]#[N:25])=[CH:19][CH:20]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 10267727HCID 10267727, compound

Product 1

HCID 22476609HCID 22476609, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

[2-hydroxy-2-(4-hydroxyphenyl)cyclohexyl][(methylethyl)sulfonyl]amine (3.40 g, 10.9 mmol), bromoacetonitrile (1.44 g, 1.1 eq) and potassium carbonate (1.80 g, 1.2 eq) were combined in acetone (20 mL) and stirred overnight at room temperature under a nitrogen atmosphere. The solution was then filtered and the filtrate was concentrated under reduced vacuum to yield 3.71 g as a brown oil. This material was purified via silica gel chromatography employing the Water's Prep. 200 while eluting with a solvent of hexane/ethyl acetate 3:2 to yield the intermediate title compound (2.52 g, 67%) as a tan solid. Ion spray M.S. 351.2 (M*−1). Calculated for C17H24N2O4S: Theory: C 57.93, H 6.86, N 7.95. Found: C 57.61, H 6.84, N 8.12.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationthe filtrate was concentrated under reduced vacuum
  3. customto yield 3.71 g as a brown oil
  4. customThis material was purified via silica gel chromatography
  5. wash200 while eluting with a solvent of hexane/ethyl acetate 3:2

Sources & evidence

ORD record
ord-db0cfe11dbc045a38a07b30643722a88
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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