Water → HCID 20397841, compound

HRID 929267Notes

Reaction equation

HRID 929267 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]=[N+:14]=[N-:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 114240934-Hydroxybenzene-1-sulfonyl chloride

Product 1

HCID 20397841HCID 20397841, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

4-hydroxybenzene sulfonyl chloride synthesized in Synthetic example 1 (3.76 g, 19.5 mmol, and 1.00 Eq) was dissolved in acetone (50 mL) and then water (50 mL) was added thereto. The obtained mixed solution was cooled to 0° C. and NaN3 (1.41 g, 21.7 mmol, and 1.11 Eq) was added to the solution slowly, followed by stirring at 0° C. for 1 hour. After the stirring, acetone was removed by the evaporator (30° C., 150 mbar) and a water layer was extracted with dichloromethane (3×30 mL). The obtained organic layer was dried with sodium sulfate and dichloromethane was removed by the evaporator. The product as oil (3.06 g, 15.4 mmol, and 79%) was dried in vacuo to obtain 4-hydroxybenzenesulfonyl azide.

Workup

  1. additionThe obtained mixed solution
  2. customAfter the stirring, acetone was removed by the evaporator (30° C., 150 mbar)
  3. extractiona water layer was extracted with dichloromethane (3×30 mL)
  4. dry with materialThe obtained organic layer was dried with sodium sulfate and dichloromethane
  5. customwas removed by the evaporator

Sources & evidence

ORD record
ord-7d93e43eb9e7492ebdff859784c56a3c
Source dataset
uspto-grants-2016_03
Patent number
US09291908B2

Reaction notes

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