Hydrochloric Acid → HCID 19009833, compound

HRID 1973541Notes

Reaction equation

HRID 1973541 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1N)([CH3:3])[CH3:2].N([O-])=O.[Na+].[ClH:18].[S:19](=[O:21])=[O:20]>C(O)(=O)C>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[S:19]([Cl:18])(=[O:21])=[O:20])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 32484DiisopropylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 19009833HCID 19009833, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

One equivalent part by weight of 2,6-diisopropylaniline is diazotized with 1.1 equivalent parts of sodium nitrite and 1.1 equivalent parts of hydrochloric acid in acetic acid at 0° to 5°. This solution is added dropwise with stirring to a solution of acetic acid containing 1 equivalent part of cuprous chloride and excess sulfur dioxide at 10°. When the addition is complete and nitrogen evolution ceases, the mixture is poured into ice water and the oily product extracted into ether. The organic layer is washed with water and dried over sodium sulfate. Removal of the solvent gives 2,6-diisopropylbenzenesulfonyl chloride which may be purified by distillation.

Workup

  1. additionThis solution is added dropwise
  2. additionWhen the addition
  3. extractionthe oily product extracted into ether
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-99b0b8eabe724c688774d9c80f47022a
Source dataset
uspto-grants-1976_12
Patent number
US03997603

Reaction notes

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