Carbon Dioxide → HCID 18787509, compound

HRID 1107516Notes

Reaction equation

HRID 1107516 reaction equation
C(N(S(F)(F)[F:7])CC)C.C(=O)=O.[CH3:13][C-:14]1[CH:18]([CH3:19])[C:17]2[CH:20]=[CH:21][CH:22]=[C:23]([CH:24]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:25]O)[C:16]=2[O:15]1.[Cl:32]C(Cl)C>CC(C)=O.O.ClCCl>[ClH:32].[CH3:13][C:14]1[O:15][C:16]2[C:23]([CH:24]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:25][F:7])=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]=1[CH3:19]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 63651,1-DichloroethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 86755395HCID 86755395, compound

Product 1

HCID 18787509HCID 18787509, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.664 ml (3.72 mmol) of diethylaminosulphur trifluoride (DAST) and 5 ml of dichloromethane are placed in a 50 ml round-bottomed flask. The mixture is cooled to -78° C. by a bath of dry ice in acetone and a solution of 0.877 g (3.38 mmol) of 2,3-dimethyl-7-(1-diethylamino-2-hydroxyethyl)benzofuran id 5 ml of dichloroethane is added dropwise. Stirring is continued for 90 minutes at this temperature, before allowing the reaction mixture to return to room temperature. 10 ml of water are added and extraction is carried out with dichloroethane (3×15 ml). The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a silica column (elution solvent: 5% methanol in dichloromethane). 700 mg (Yield: 62%) of 2,3-dimethyl-7-(1-diethylamino-2-fluoroethyl)benzofuran hydrochloride are obtained in the form of a colourless oil.

Workup

  1. customto return to room temperature
  2. extractionextraction
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by chromatography on a silica column (elution solvent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5c713589115d451f9f72bfe498df55ee
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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