Hydrochloric Acid → HCID 13493454, compound

HRID 660690Notes

Reaction equation

HRID 660690 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17].Cl>CN(C=O)C>[C:3]1([S:9][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 784911-Butanol, 4-bromo-, 1-acetate

Product 1

HCID 13493454HCID 13493454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60%, 0.91 g, 23 mmol) in anhydrous DMF (20 mL) at RT is added dropwise benzenethiol (2.5 g, 22.7 mmol) in DMF (5 mL). The mixture is stirred for 10-15 min, at which time it becomes clear and yellow. The mixture is cooled to 0° C. in an ice bath then 4-bromobutylacetate (4.5 g, 22.8 mmol) in DMF (5 mL) is added dropwise and the mixture is stirred at RT for 1 h. The mixture is poured into 1N HCl (50 mL) and extracted with MTBE (2×). The combined organic extracts are washed with brine (2×) and dried over MgSO4. The solvent is removed under reduced pressure to afford the title compound as a yellow oil.

Workup

  1. stirringthe mixture is stirred at RT for 1 h
  2. extractionextracted with MTBE (2×)
  3. washThe combined organic extracts are washed with brine (2×)
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-3c9ef9c46b974665ad06ede48cc8a136
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…