Isobutyl mercaptan → N-(5-tert-butyl-isoxazol-3-yl)-2-isobutylsulfanyl-2-methyl-propionamide

HRID 73234Notes

Reaction equation

HRID 73234 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][SH:4].[OH-].[K+].Br[C:9]([CH3:23])([CH3:22])[C:10]([NH:12][C:13]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[O:15][N:14]=1)=[O:11]>C(O)C>[C:18]([C:16]1[O:15][N:14]=[C:13]([NH:12][C:10](=[O:11])[C:9]([S:4][CH2:3][CH:2]([CH3:5])[CH3:1])([CH3:22])[CH3:23])[CH:17]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 10558Isobutyl mercaptanHCID 14797Potassium HydroxideHCID 596626262-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide

Product 1

HCID 59703993N-(5-tert-butyl-isoxazol-3-yl)-2-isobutylsulfanyl-2-methyl-propionamideYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 82 μL (1.31 mmol) of 2-methyl-1-propanethiol in ethanol (2 mL) were added 37 mg (0.65 mmol) of KOH pellets, followed by 190 mg (0.65 mmol) 2-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide (prepared as described in step 2, method B). 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 to yield 160 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-isobutylsulfanyl-2-methyl-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

Sources & evidence

ORD record
ord-7fb13c4b14514bb9bb6e7d291455b61f
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

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