Potassium Carbonate → HCID 9804889, compound

HRID 2181567Notes

Reaction equation

HRID 2181567 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].C1(S)CCCCC1>CN(C=O)C.O>[ClH:1].[CH:25]1([S:24][C:21]2[CH:20]=[CH:19][C:18]([S:15]([C:6]3([C:4]([NH:3][OH:2])=[O:5])[CH2:7][CH2:8][N:9]([CH2:12][C:13]#[CH:14])[CH2:10][CH2:11]3)(=[O:17])=[O:16])=[CH:23][CH:22]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 9890734HCID 9890734, compound

Product 1

HCID 9804889HCID 9804889, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of the propargyl amine of Example 9, part F (6.5 g, 18.4 mmol) in DMF (10 mL) were added potassium carbonate (3.81 g, 27.6 mmol) and cyclohexyl mercaptan (3.37 mL, 27.6 mmol). The solution was heated to 100 degrees Celsius for 6.5 hours. The solution was diluted with H2O and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate. Chromatography (on silica, hexane/ethyl acetate) provided the sulfide as a yellow oil (6.05 g, 73%).

Workup

  1. temperatureThe solution was heated to 100 degrees Celsius for 6.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over magnesium sulfate

Sources & evidence

ORD record
ord-5b400ecba9e04015ab3ee75eee6c952a
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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