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

HRID 651082Notes

Reaction equation

HRID 651082 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 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 0.146 g (1.0 mmol) of the product of Example 87 in 0.3 mL of dichloromethanein 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 0.130 mg (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-2efefba626904a97ae6118205a5a8112
Source dataset
uspto-grants-2001_08
Patent number
US06277885B1

Reaction notes

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