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

HRID 353549Notes

Reaction equation

HRID 353549 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN(C=O)C.[Na+].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O-:27])(=O)=[O:25])=[CH:20][CH:19]=1)[C:14]#[C:15][CH3:16]>C(Cl)Cl>[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([Cl:4])(=[O:27])=[O:25])=[CH:20][CH:19]=1)[C:14]#[C:15][CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 237040564-But-2-ynyloxy-benzenesulfonic acid sodium salt

Product 1

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of oxalyl chloride (47.8 ml, 0.545 mol) at 0° C. in 240 mL of CH2Cl2 was added a DMF (43.0 ml) solution of 4-but-2-ynyloxy-benzenesulfonic acid sodium salt in a drop wise manner. The reaction mixture was stirred at 0° C. for 30 min and then let warm to room temperature and stirred for 18 h. The reaction was then poured into ice and extracted with hexanes. The organics were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to provide 42.0 g (95%) of the desired product as yellow solid.

Workup

  1. temperaturelet warm to room temperature
  2. stirringstirred for 18 h
  3. additionThe reaction was then poured into ice
  4. extractionextracted with hexanes
  5. washThe organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a54bc231ffe42e2be5fe7c6753c0f3c
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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