Dimethylformamide → 4-But-2-ynyloxy-benzenesulfonyl chloride

HRID 2084834Notes

Reaction equation

HRID 2084834 reaction equation
[C:1]([O:5][C:6]#[C:7][CH2:8][CH3:9])#[C:2][CH2:3][CH3:4].[Cl:10][S:11]([OH:14])(=O)=[O:12].[C:15](Cl)(=O)[C:16](Cl)=O.CN(C=O)C>ClCCl.CCCCCC>[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([S:11]([Cl:10])(=[O:14])=[O:12])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chlorideHCID 54210684HCID 54210684, compound

Product 1

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 0.146 g (1.0 mmol) of the product of Example 3 in 0.3 mL of dichloromethane in an acetone/ice bath under N2 was dropwise added a solution of 0.073 mL (1.1 mmol) of chlorosulfonic acid in 0.3 mL of dichloromethane. After the addition was complete, the ice bath was removed and the reaction was stirred at room temperature for 2 h. To the reaction was then dropwise added 0.113 mL (1.3 mmol) of oxalyl chloride, followed by 0.015 mL DMF. The reaction was heated to reflux for 2 h and then diluted with hexane and poured into ice water. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 0.130mg (53%) of the desired product as a light brown solid.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 2 h
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5d1282a1cb846d1893dc6a3af0b4ba9
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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