Dimethylformamide → HCID 53673532, compound

HRID 650857Notes

Reaction equation

HRID 650857 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:8][S:9](=[S:12])([O-:11])=[O:10].[Na+].CN(C=O)C>O>[CH3:8][S:9](=[S:12])([O:11][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 81011-BromohexaneHCID 23688755Methanesulfonothioic acid, sodium salt

Product 1

HCID 53673532HCID 53673532, compoundYield 165%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The reaction mixture of 1-bromohexane (1.046 g, 0.00635 mol), sodium methanethiosulfonate (0.850 g, 0.00635 mol) and dry DMF (6 mL) was heated at 60° C. for 2 hr. At room temperature, water (15 mL) was added and the resulting mixture was extracted with ether (3×30 mL). The extracts were washed with brine, dried, concentrated and the residue was subjected to flash column chromatography on silica gel with EtOAc-hexanes (1:4) to afford a colorless liquid (2.057 g, 82%). IR (CDCl3 cast): 3030 (w), 3010 (w), 2955 (st), 2930 (st), 2860 (st), 1460 (m), 1320 (st), 1133 (st), 955 (st), 747 cm−1 (st); 1H NMR (200 MHz, CDCl3): δ 3.33 (s, 3H, CH3SO2S), 3.18 (t, J=7.4 Hz, 2H, SCH2CH2), 1.77 (pseudo p, J=7.2 Hz, 2H, SCH2CH2), 1.50-1.20 (m, 6H, CH2CH2CH2CH3), 0.90 (m, 3H, CH2CH3); 13C NMR (50 MHz, CDCl3): δ 50.64, 36.50, 31.13, 29.46, 28.26, 22.44, 13.96.

Workup

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

Sources & evidence

ORD record
ord-9cedfdb562404ff1b25e10467472c027
Source dataset
uspto-grants-2001_08
Patent number
US06277617B1

Reaction notes

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