Potassium Hydroxide → N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(thiophen-2-ylsulfanyl)-propionamide

HRID 2069496Notes

Reaction equation

HRID 2069496 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].[OH-].[K+].Br[C:10]([CH3:24])([CH3:23])[C:11]([NH:13][C:14]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[O:16][N:15]=1)=[O:12]>C(O)C>[C:19]([C:17]1[O:16][N:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]([CH3:23])([S:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH3:24])[CH:18]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5226742-ThiophenethiolHCID 596626262-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide

Product 1

HCID 59662681N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(thiophen-2-ylsulfanyl)-propionamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.16 mL (1.7 mmol) of thiophene-2-thiol in ethanol (5 mL) were added 102 mg (1.8 mmol) of KOH pellets, followed by 460 mg (1.6 mmol) 2-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide (prepared as described in step 1, method C). The reaction mixture was heated to reflux for 18 h. The reaction was cooled to room temperature. The solid (KBr) was separated by filtration and rinsed with ethanol (15 mL). The filtrate was concentrated under reduced pressure and the residue purified by column chromatography (silica, eluent: heptanes, 0-10% ethyl acetate) to yield 504 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(thiophen-2-ylsulfanyl)-propionamide.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe solid (KBr) was separated by filtration
  4. washrinsed with ethanol (15 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by column chromatography (silica, eluent: heptanes, 0-10% ethyl acetate)

Sources & evidence

ORD record
ord-b9524683ae9d44cfaf9439d0df4d8c41
Source dataset
uspto-grants-2012_10
Patent number
US08299111B2

Reaction notes

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