Potassium Carbonate → 2-(4-t-Butylphenylthio)ethylamine

HRID 1010512Notes

Reaction equation

HRID 1010512 reaction equation
Cl.Cl[CH2:3][CH2:4][NH2:5].C([O-])([O-])=O.[K+].[K+].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([S:22][CH2:3][CH2:4][NH2:5])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754544-Tert-ButylbenzenethiolHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 136820922-(4-t-Butylphenylthio)ethylamineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring mixture of 4.36 g (38.0 mmol) of 2-chloroethylamine hydrochloride and 12.00 g (87.0 mmol) of K2CO3 in 30 mL of CHCl3 was added 4.82 g (29.0 mmol) of 4-t-butylbenzenethiol. The mixture was stirred at 50° C. in a sealed vial overnight. The mixture was washed three times with distilled water, dried with MgSO4 and filtered. Volatiles were removed in vacuo leaving 4.50 g (74%) of clear oil. 1H NMR (300 MHz, CDCl3): δ=7.32, m, 4H, 2.93, m, 4H, 1.42, broad singlet, 2H, 1.30, s, 9H.

Workup

  1. washThe mixture was washed three times with distilled water
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-54ef78cf6aba4038b67f143af5661768
Source dataset
uspto-grants-2011_07
Patent number
US07977269B2

Reaction notes

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