Dimethyl Sulfoxide → HCID 68691865, compound

HRID 1157796Notes

Reaction equation

HRID 1157796 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=[S:9].[C:23](=O)([O-])[O-].[K+].[K+].IC.CS(C)=O>C(OCC)(=O)C>[CH3:23][S:9][C:8](=[N:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86615861HCID 86615861, compound

Product 1

HCID 68691865HCID 68691865, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Part B: A mixture of tert-butyl 4-(pyridin-2-ylcarbamothioyl)piperazine-1-carboxylate (15.30 g, 47.5 mmol), potassium carbonate (13.10 g, 95.0 mmol), iodomethane (3.00 mL, 47.5 mmol), and DMSO (200 mL) was stirred at 25° C. for 24 h. The reaction mixture was diluted with ethyl acetate, washed with water (×4) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated to provide tert-butyl 4-(methylthio(pyridin-2-ylimino)methyl)piperazine-1-carboxylate (12.00 g) as a waxy solid; 1H NMR (300 MHz, CDCl3) δ 8.25 (m, 1H), 7.63 (m, 1H), 6.88 (m, 2H), 3.70 (m, 4H), 3.52 (m, 4H), 2.04 (s, 3H), 1.44 (s, 9H).

Workup

  1. washwashed with water (×4) and brine
  2. customdried over anhyd
  3. filtrationsodium sulfate, filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a9d4dee3d76413ea345d8ead5a98f1c
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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