Hydrochloric Acid → 1,3-Dihydro-4-isobenzofuransulfonyl chloride

HRID 483054Notes

Reaction equation

HRID 483054 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](N)[C:4]=2[CH2:3][O:2]1.[N+]([O-])([O-])=O.[Na+].[S:16](=[O:18])=[O:17].[ClH:19]>C(O)(=O)C.O.O.O.[Cu](Cl)Cl>[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:16]([Cl:19])(=[O:18])=[O:17])[C:4]=2[CH2:3][O:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1119Sulfur DioxideHCID 24268Sodium Nitrate2×HCID 134722524-Amino-1,3-dihydroisobenzofuran

Product 1

HCID 134722541,3-Dihydro-4-isobenzofuransulfonyl chloride

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A suspension of 22.1 g of the crude hydrochloride salt prepared in Example 2 in a mixture of 30 ml of concentrated hydrochloric acid and 30 ml acetic acid was cooled to 0°-5°. A solution of 6.2 g of sodium nitrate in 15 ml water was added dropwise at 0°-5°. The thick suspension was diluted with 19 ml of concentrated hydrochloric acid to facilitate stirring and 1.0 g of sodium nitrate was added; stirring was continued for 1 hour. The suspension of the diazonium salt was added portionwise at 0°-5° to a stirred mixture of 80 ml of acetic acid, 25 ml of sulfur dioxide and 1.6 g of copper (II) chloride dihydrate. The resulting pale green suspension was allowed to warm to ambient temperature and stirred for 4.5 hours. The yellow-green solution was poured into 1000 ml of cold water and the aqueous mixture extracted three times with 1-chlorobutane. The combined organic solution was washed three times with water and saturated sodium bicarbonate solution, then dried over magnesium sulfate, and filtered. Evaporation of the solvent in vacuo gave 9.8 g of 1,3-dihydrobenzo[c]furan-4-sulfonyl chloride as a yellow oil which crystallized on cooling and scratching, m.p. 40°-43°.

Workup

  1. temperaturewas cooled to 0°-5°
  2. stirringstirring
  3. stirringstirred for 4.5 hours
  4. extractionthe aqueous mixture extracted three times with 1-chlorobutane
  5. washThe combined organic solution was washed three times with water and saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-e163efd917e24a14bd058d033ff9ffc4
Source dataset
uspto-grants-1986_03
Patent number
US04578108

Reaction notes

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