1,2-Dimethoxyethane → HCID 23028562, compound

HRID 748713Notes

Reaction equation

HRID 748713 reaction equation
C(COC)OC.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Na+].Br[CH2:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>CCOCC>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:19][C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[C:22]#[N:23])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 895992-(Bromomethyl)benzonitrileHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 23028562HCID 23028562, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A dimethoxyethane (5 ml) suspension of sodium 4-chlorobenzenesulfinate (218 mg, 1.10 mmol) and 2-bromomethylbenzonitrile (215 mg, 1.10 mmol) was stirred at 70° C. for 17 hours. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure. The residue thus obtained was subjected to chromatography on a short silica gel column and the fraction obtained from the ether eluate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and the fraction obtained from the hexane:ethyl acetate (=3:1) eluate was concentrated under reduced pressure to give a white solid. The resulting white solid was washed with ether, and collected by filtration, whereby the title compound (226 mg, 70%) was obtained as a white powder.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationwas concentrated under reduced pressure
  5. customthe fraction obtained from the hexane
  6. concentrationethyl acetate (=3:1) eluate was concentrated under reduced pressure
  7. customto give a white solid
  8. washThe resulting white solid was washed with ether
  9. filtrationcollected by filtration, whereby the title compound (226 mg, 70%)
  10. customwas obtained as a white powder

Sources & evidence

ORD record
ord-af77017f93d54aa0a08da286258dec19
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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