Potassium Carbonate → Toluene-4-thiosulfonic acid S-[3(ethylisopropylamino)-propyl]ester

HRID 707676Notes

Reaction equation

HRID 707676 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH2:16]([NH:18][CH:19]([CH3:21])[CH3:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:16]([N:18]([CH:19]([CH3:21])[CH3:20])[CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 88318IsopropylethylamineHCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Product 1

HCID 67606220Toluene-4-thiosulfonic acid S-[3(ethylisopropylamino)-propyl]ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Toluene-4-thiosulfonic acid S-(3-chloro-propyl) ester (12.0 g, 45.3 mol, 1.00 eq.), N-ethylisopropylamine (4.2 g, 48.0 mmol, 1.05 eq.) and potassium carbonate (6.9 g, 49.9 mmol, 1.10 eq.) were stirred together in acetonitrile (160 mL) at 60° C. for 18 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (250 mL). The organic solution was washed with brine (250 mL), dried (MgSO4) and the resulting oil was purified by MPLC chromatography to give an oil weighing 2.98 g (21%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (250 mL)
  3. washThe organic solution was washed with brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. customthe resulting oil was purified by MPLC chromatography
  6. customto give an oil

Sources & evidence

ORD record
ord-795a681f2d07409491848ad636f447b5
Source dataset
uspto-grants-2015_11
Patent number
US09175042B2

Reaction notes

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