Water → 2-Aminoresorcinol ditosylate

HRID 337342Notes

Reaction equation

HRID 337342 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].C(N([CH2:15][CH3:16])CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[OH2:28]>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][S:23]([C:20]3[CH:21]=[CH:22][C:15]([CH3:16])=[CH:18][CH:19]=3)(=[O:24])=[O:28])[C:2]=2[NH2:1])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 694512-Aminoresorcinol

Product 1

HCID 867032532-Aminoresorcinol ditosylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg of 2-aminobenzene-1,3-diol was dissolved in 2 ml of dichloromethane, and 234 μl of triethyl amine and 320 mg of p-toluene sulfonyl chloride were added and stirred at room temperature for 1.5 hours. To the reaction mixture, 20 ml of water was added, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to yield 278.1 mg of the title compound.

Workup

  1. extractionextracted with 20 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2d8aa5891f7b4dbcbda57d5c695a9ac8
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…