Dimethyl Sulfoxide → 4-(4-(2-Amino-2-methylpropyl)phenoxy)benzamide

HRID 2227753Notes

Reaction equation

HRID 2227753 reaction equation
OO.[NH2:3][C:4]([CH3:22])([CH3:21])[CH2:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1.C([O-])([O-])=[O:24].[K+].[K+].CS(C)=O>O>[NH2:3][C:4]([CH3:22])([CH3:21])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]([NH2:16])=[O:24])=[CH:13][CH:12]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 221477714-(4-(2-Amino-2-methylpropyl)phenoxy)benzonitrile

Product 1

HCID 118329614-(4-(2-Amino-2-methylpropyl)phenoxy)benzamideYield 169.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous 30% H2O2 (62.1 mL, 548 mmol) was added dropwise to a mixture of 4-(4-(2-amino-2-methylpropyl)phenoxy)benzonitrile (53.2 g, 200 mmol), K2CO3 (15.78 g, 114 mmol) and DMSO (270 mL) over 20 min while the temperature was held at 20° C. with a cooling bath. The mixture was stirred at this temperature for 1 h after the addition was complete, and then water (209 mL) was added slowly. The slurry was cooled in an ice bath with stirring for 1 h, and the product was then filtered, washed with water and dried in vacuo at 50° C. to yield 55.0 g (97%) of white solid. Analysis by HPLC indicated purity of >99%. NMR.

Workup

  1. customwas held at 20° C. with a cooling bath
  2. additionafter the addition
  3. temperatureThe slurry was cooled in an ice bath
  4. stirringwith stirring for 1 h
  5. filtrationthe product was then filtered
  6. washwashed with water
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-44bab833b5cc472c81c89ac5d4945023
Source dataset
uspto-grants-2002_07
Patent number
US06413991B1

Reaction notes

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