Triethylamine → 3,4-Bis(acetyloxy)benzenesulfonyl chloride

HRID 2051161Notes

Reaction equation

HRID 2051161 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([S:15]([OH:18])(=O)=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].CN(C)C(=O)C.C(N(CC)CC)C.P(Cl)(Cl)([Cl:34])=O>S1(CCCC1)(=O)=O.C(#N)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([S:15]([Cl:34])(=[O:18])=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 13723669HCID 13723669, compound

Product 1

HCID 190224303,4-Bis(acetyloxy)benzenesulfonyl chlorideYield 74%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the crude, 3,4-diacetoxy benzene sulphonic acid (0.83 g) in a mixture of sulpholane (1.5 ml) and acetonitrile (1.5 ml) was added at room temperature successively N,N-dimethylacetamide (75 μl), triethylamine (0.85 ml) and phosphorus oxychloride (1.1 ml). The reaction mixture was thereafter heated for 15 minutes at 70° C., cooled, poured onto water and extracted with CH2Cl2. The extract was dried over magnesium sulphate, concentrated and chromatographed on silica gel (50 g). Elution with CH2Cl2 gave 0.65 g (74%) of the title compound as a white solid. NMR in CDCl3 : 2.33(s,6H); 7.29(d,1H); 7.90(s,1H); 7.95(dd,1H).

Workup

  1. temperaturecooled
  2. additionpoured onto water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extract was dried over magnesium sulphate
  5. concentrationconcentrated
  6. customchromatographed on silica gel (50 g)
  7. washElution with CH2Cl2

Sources & evidence

ORD record
ord-e9e7ba2d700a4b029bd0c41f01069c86
Source dataset
uspto-grants-1991_05
Patent number
US05017569

Reaction notes

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