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

HRID 2287018Notes

Reaction equation

HRID 2287018 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

Conditions

Temperature
40 °C

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. 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 100 ml of water and air-dried. Yield:56 g; Melting Point: 74°-74.5° C.

Workup

  1. customas described in Synthesis Example 1
  2. additionAfter completion of the addition
  3. stirringwith stirring until it
  4. temperaturecooled to room temperature
  5. stirringstirred for 30 minutes
  6. customthe crystals thus precipitated
  7. filtrationwere collected by filtration
  8. washThe crystals were washed with 100 ml of water
  9. customair-dried

Sources & evidence

ORD record
ord-d2145acb05ea467eaec42e273de0558b
Source dataset
uspto-grants-1981_05
Patent number
US04268624

Reaction notes

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