Sulfuric Acid → 1-Benzenesulfonyl-1,2-dicarbisopropoxy hydrazine

HRID 46920

Reaction equation

HRID 46920 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].S(=O)(=O)(O)O.C1(S(O)=O)C=CC=CC=1.[N:25]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])=[N:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28]>O>[C:1]1([S:7]([N:25]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[NH:26][C:27]([O:29][CH:30]([CH3:31])[CH3:32])=[O:28])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 12057Benzenesulfinic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 203859261-Benzenesulfonyl-1,2-dicarbisopropoxy hydrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To one-half mole of sodium benzenesulfinate in water in a 2 liter beaker is introduced 49 g (0.5 mole) of concentrated sulfuric acid. To the resulting suspension of benzenesulfinic acid is then added 101 g (0.5 mole) of diisopropyl azodicarboxylate. The mixture is stirred and heated to 60° C. (30 minutes). The yellow color of the azo ester gradually disappears. The oily product is extracted with benzene and separated from the lower aqueous layer. Removal of the benzene by evaporation leaves a clear oil which crystallizes when introduced into an 80/20 hexane/benzene mixture. The filtered crystals are dried at 60° C.

Workup

  1. extractionThe oily product is extracted with benzene
  2. customseparated from the lower aqueous layer
  3. customRemoval of the benzene
  4. customby evaporation
  5. customleaves a clear oil which
  6. customcrystallizes when
  7. additionintroduced into an 80/20 hexane/benzene mixture
  8. customThe filtered crystals are dried at 60° C.

Sources & evidence

ORD record
ord-58cd4acef3d14a2cb43d04d5449aeec1
Source dataset
uspto-grants-1979_11
Patent number
US04175200

Linked notes

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