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

HRID 2287012Notes

Reaction equation

HRID 2287012 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>CN(C)C(=O)C>[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. 75 ml of N,N-dimethylacetamide was added dropwise to the mixture with stirring while the reaction mixture was maintained at 30° to 40° C. After completion of the addition, the mixture was allowed to stand with stirring until it cooled to room temperature (about 20°-25° C.). The reaction mixture was then poured into 600 ml of ice water, stirred for 30 minutes and the crystals thus-precipitated were collected by filtration. The crystals were washed with water and air-dried. Yield: 56 g; Melting Point: 74° to 74.5° C.

Workup

  1. customas described in Synthesis Example 1
  2. temperaturewas maintained at 30° to 40° C
  3. additionAfter completion of the addition
  4. stirringwith stirring until it
  5. stirringstirred for 30 minutes
  6. customthe crystals thus-precipitated
  7. filtrationwere collected by filtration
  8. washThe crystals were washed with water
  9. customair-dried

Sources & evidence

ORD record
ord-09613f48063f43cc98adf613132e867a
Source dataset
uspto-grants-1981_05
Patent number
US04268625

Reaction notes

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