Acetone → 2-(2-Methoxyethoxy)-5-nitrobenzenesulfonyl chloride

HRID 224576Notes

Reaction equation

HRID 224576 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[S:15]([O-:18])(=O)=[O:16].[Na+].CC(C)=O.P(Cl)(Cl)([Cl:26])=O>CC(N(C)C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[S:15]([Cl:26])(=[O:18])=[O:16]

Participants

5

Reactant 3

HCID 180AcetoneHCID 24813Phosphorus oxychlorideHCID 101686797CID 101686797

Product 1

HCID 129314372-(2-Methoxyethoxy)-5-nitrobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

59 g of sodium 2-(2-methoxyethoxy)-5-nitrobenzenesulfonate prepared as described in Synthesis Example 1 was added to a mixture of 200 ml of acetone and 75 ml of phosphorous oxychloride and 75 ml of dimethylacetamide was added dropwise to the mixture with stirring while the reaction mixture was maintained at 30° to 40° C. After completion of the dropwise addition, the reaction mixture was allowed to stand while stirring until it cooled to room temperature. The reaction mixture was then poured into 600 ml of ice water, stirred for 30 minutes and the crystals thus-precipitated were recovered by filtration. The crystals were washed with 100 ml of water and air-dired.

Workup

  1. customas described in Synthesis Example 1
  2. additionwas added dropwise to the mixture
  3. temperaturewas maintained at 30° to 40° C
  4. additionAfter completion of the dropwise addition
  5. stirringwhile stirring until it
  6. stirringstirred for 30 minutes
  7. customthe crystals thus-precipitated
  8. filtrationwere recovered by filtration
  9. washThe crystals were washed with 100 ml of water

Sources & evidence

ORD record
ord-fb974f888a6d4bff9c2d02913d0bbdab
Source dataset
uspto-grants-1980_11
Patent number
US04233237

Reaction notes

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