Hydrochloric Acid → HCID 67980801, compound

HRID 2406933Notes

Reaction equation

HRID 2406933 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13]S(C(C)(C)C)=O)[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[ClH:20].O1CCOCC1>CO>[ClH:20].[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH2:13])[CH2:9][CH:10]([CH3:11])[CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67981151HCID 67981151, compound

Product 1

HCID 67980801HCID 67980801, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-(4-iodophenyl)-3-methylbutyl)-2-methylpropane-2-sulfinamide (1.36 g, 3.45 mmol) was dissolved in methanol (17.2 mL). 4M HCl in dioxane (4.31 mL, 17.2 mmol) was added and the reaction was stirred at room temperature for 1 hour. The reaction was concentrated and the resulting solid was triturated with ether and dried under vacuum to provide 1-(4-iodophenyl)-3-methylbutan-1-amine hydrochloride (1.1 g, 100%) as a white solid. 1H NMR (400 MHz, CD3OD, δ): 7.80-7.84 (m, 2H), 7.20-7.24 (m, 2H), 4.25-4.31 (m, 1H), 1.83-1.92 (m, 1H), 1.71-1.79 (m, 1H), 1.34-1.42 (m, 1H), 0.92 (dd, J=12.19, 6.54 Hz, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting solid was triturated with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0c49c4d75cd944ca95d14cdd6a22ce8a
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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