Dimethylformamide → HCID 22457522, compound

HRID 2184707Notes

Reaction equation

HRID 2184707 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([O-:20])(=O)=[O:18])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[K+].CN(C)C=O.S(Cl)([Cl:29])=O>>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([Cl:29])(=[O:20])=[O:18])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23713435HCID 23713435, compound

Product 1

HCID 22457522HCID 22457522, compoundYield 80.4%

Conditions

Temperature
80 °C

Procedure

Potassium 4-(2-acetoxy-ethyl)-naphthalene-1-sulfonate (102.3 g, 308 mmol) was added in portions over 15 minutes to a room temperature solution of dimethylformamide (2.4 mL, 31 mmol) in thionyl chloride (112 mL, 1.54 mol). The reaction mixture was gradually brought to 80° C. (oil bath temperature) over 30 minutes and heated at 80° C. for 90 minutes, then cooled to room temperature and stirred at room temperature for 60 minutes. The reaction mixture was partitioned between ice water (500 mL) and ethyl acetate (500 mL). The organic layer was washed with water (200 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to a cream colored solid. The crude product was triturated with pet ether to afford 4-(2-acetoxy-ethyl)-naphthalene-1-sulfonyl chloride as a pale tan solid (77.47 g).

Workup

  1. customwas gradually brought to 80° C.
  2. customover 30 minutes
  3. temperaturecooled to room temperature
  4. customThe reaction mixture was partitioned between ice water (500 mL) and ethyl acetate (500 mL)
  5. washThe organic layer was washed with water (200 mL) and brine (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum to a cream
  9. customThe crude product was triturated with pet ether

Sources & evidence

ORD record
ord-d1cd708de4474c4894bdd0344daea232
Source dataset
uspto-grants-2002_06
Patent number
US06399597B1

Reaction notes

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