p-Toluenesulfonyl azide → HCID 21938930, compound

HRID 2288568Notes

Reaction equation

HRID 2288568 reaction equation
[CH:1]1([S:7]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C1(C)C=CC(S([N:33]=[N+:34]=[N-])(=O)=O)=CC=1>C(O)C.O>[CH:1]1([S:7]([C:10]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[N+:33]=[N-:34])(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 13661p-Toluenesulfonyl azideHCID 14798Sodium HydroxideHCID 18699519HCID 18699519, compound

Product 1

HCID 21938930HCID 21938930, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

3.0 g of the cyclohexylsulfonyl-(4-methoxyphenylsulfonyl)methane prepared in (2), was put into a flask, and 100 mL of ethanol was added thereto, followed by stirring. Further, to this solution, 8.0 g of a 5 wt % ethanol solution of sodium hydroxide was added, followed by stirring. This reaction solution was cooled to from -5° C. to -10° C., and 35 mL of pure water was added thereto. Then, 10 mL of the ethanol solution containing 2.0 g of p-toluenesulfonylazide obtained in Reference Example 2, was dropwise added thereto over a period of 5 minutes, and the mixture was stirred for 3 hours and left to stand overnight. Then, the precipitate was collected by filtration to obtain crude crystals. The crude crystals were re-crystallized from ethanol to obtain cyclohexylsulfonyl-(4-methoxyphenylsulfonyl)diazomethane.

Workup

  1. customwas put into a flask
  2. stirringby stirring
  3. additionwas added
  4. customobtained in Reference Example 2
  5. additionwas dropwise added
  6. stirringthe mixture was stirred for 3 hours
  7. waitleft
  8. waitto stand overnight
  9. filtrationThen, the precipitate was collected by filtration
  10. customto obtain crude crystals
  11. customThe crude crystals were re-crystallized from ethanol

Sources & evidence

ORD record
ord-cdd7f61155764e3eb4bdc7405af2b10f
Source dataset
uspto-grants-2000_07
Patent number
US06090518

Reaction notes

Loading…