4-Toluenesulfonyl chloride → HCID 11175590, compound

HRID 982303Notes

Reaction equation

HRID 982303 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].C1(NC2CCCCC2)CCCCC1>CC(C)=O>[S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)([O:7][CH2:6][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=[CH:9][C:8]=1[N+:12]([O-:14])=[O:13])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7582DicyclohexylamineHCID 119332(2,6-Dinitrophenyl)methanol3×

Product 1

HCID 11175590HCID 11175590, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution was prepared containing 2 grams of the 2,6-dinitrobenzyl alcohol and 2.37 grams of tosyl chloride in 15 ml of dry acetone (20 degrees Centigrade). A solution of dicyclohexyl amine (2.25 ml in 5 ml of dry acetone) was added dropwise to the 2,6-dinitrobenzyl alcohol mixture. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then treated as described above for the preparation of 2,6-dinitrobenzyl alcohol. After recrystallization, 2.3 grams of 2,6-dinitrobenzyl tosylate was obtained.

Workup

  1. customA solution was prepared
  2. additionThe reaction mixture was then treated
  3. customAfter recrystallization

Sources & evidence

ORD record
ord-3245b20c4bbf43fc970ac19d9967384a
Source dataset
uspto-grants-1991_02
Patent number
US04996136

Reaction notes

Loading…