Water → HCID 53665013, compound

HRID 650855Notes

Reaction equation

HRID 650855 reaction equation
Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:7][S:8](=[S:11])([O-:10])=[O:9].[Na+].O>CN(C=O)C>[CH3:7][S:8](=[S:11])([O:10][CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 78911-Bromo-3-methylbutaneHCID 23688755Methanesulfonothioic acid, sodium salt

Product 1

HCID 53665013HCID 53665013, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The reaction mixture of 1-bromo-3-methylbutane (1.7520 g, 0.0116 mol) and sodium methanethiosulfonate (1.554 g, 0.0116 mol) in dry DMF (5 mL) was heated at 50° C. for 2 hr. At room temperature, water (15 mL) was added and the mixture was extracted with ether (3×30 mL). The combined extracts were washed with brine, dried, concentrated. The residue was subjected to flash column chromatography on silica gel with EtOAc-hexanes (1:4). The product was obtained as a colorless liquid (1.4777 g, 70%). IR (film): 3030 (w), 3011 (w), 2958 (st), 2932 (st), 2873 (st), 1468 (m), 1410 (w), 1388 (w), 1367 (w), 1319 (st), 1136 (st), 955 (st), 748 cm−1 (st); 1H NMR (200 MHz, CDCl3): δ 3.33 (s, 3H, CH3SO2S); 3.19 (t, J=7.1 Hz, 2H, SCH2CH2), 1.70-1.58 (m, 3H, SCH2CH2CHMe2), 0.95 (d, J=5.3 Hz, 6H, CHMe2); 13C NMR (50 MHz, CDCl3): δ 50.60, 38.19, 34.59, 27.40, 22.06.

Workup

  1. extractionthe mixture was extracted with ether (3×30 mL)
  2. washThe combined extracts were washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbee6162d7414f5d9b332d55a2cad0ce
Source dataset
uspto-grants-2001_08
Patent number
US06277617B1

Reaction notes

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