4-Aminophenol → HCID 53303292, compound

HRID 871841Notes

Reaction equation

HRID 871841 reaction equation
[NH2:1][C:2]1[N:15]([CH2:16][CH3:17])[C:6]2[N:7]=[C:8](S(C)(=O)=O)[N:9]=[CH:10][C:5]=2[C:4](=[O:18])[C:3]=1[C:19]([NH2:21])=[O:20].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>CS(C)=O>[NH2:1][C:2]1[N:15]([CH2:16][CH3:17])[C:6]2[N:7]=[C:8]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:9]=[CH:10][C:5]=2[C:4](=[O:18])[C:3]=1[C:19]([NH2:21])=[O:20]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 67325100HCID 67325100, compound

Product 1

HCID 53303292HCID 53303292, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 0.40 g (1.29 mmol) of the product obtained in step 1.5 in 4 mL of anhydrous DMSO is added 0.160 g (1.47 mmol) of 4-aminophenol. The reaction mixture is heated at 110°C. overnight and then evaporated to dryness. The solid residue is purified by chromatography on silica gel, eluting with a dichloromethane/methanol gradient (100/0 to 90/10). 0.090 g of the expected product is obtained in the form of an off-white solid. Yield=20%. m.p. >260°C. M+H+=341.

Workup

  1. customevaporated to dryness
  2. customThe solid residue is purified by chromatography on silica gel
  3. washeluting with a dichloromethane/methanol gradient (100/0 to 90/10)

Sources & evidence

ORD record
ord-b07e69cfd6ff45d49dd5e90be57c35bb
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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