Cesium carbonate → Hydrochloric Acid

HRID 1917061Notes

Reaction equation

HRID 1917061 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[ClH:10].[Cl:11][CH2:12][CH2:13][NH2:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[ClH:11].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:12][CH2:13][NH2:14])=[CH:5][CH:4]=1.[ClH:10]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 127654-MethoxybenzenethiolHCID 97937372-Chloroethylamine hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 122619332-(4-Methoxyphenylthio)ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methoxybenzenethiol (25 g), 2-chloroethylamine HCl (1.1 eq.) and Cs2CO3 (2.4 eq.) in DMF (200 mL) was stirred at 60° C. for 2 days. The solvents were removed by evaporation under reduced pressure and the crude product was dissolved in 300 mL of EtOAc. The organic phase was washed with H2O (2×50 mL) and concentrated under reduced pressure. The residue was dissolved in 200 mL 1N HCl and washed with EtOAc (2×50 ml). Evaporation of the aqueous phase gave the desired product as HCl salt and white solid. Yield: 34.8 g, 91%. (The free amine can be obtained by treatment of the salt with 1N NaOH).

Workup

  1. customThe solvents were removed by evaporation under reduced pressure
  2. dissolutionthe crude product was dissolved in 300 mL of EtOAc
  3. washThe organic phase was washed with H2O (2×50 mL)
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 200 mL 1N HCl
  6. washwashed with EtOAc (2×50 ml)
  7. customEvaporation of the aqueous phase

Sources & evidence

ORD record
ord-ac158d4c7cb5468b9f9057298d98ac1c
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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